The episode begins with the host Jubin, a partner at Kleiner Perkins, introducing the show and today's guest, Yamini Rangan, CEO of HubSpot.

"Welcome to Grit, I'm Jubin, partner at Kleiner Perkins, a show where we go beyond the highlight reel and explore the personal and professional challenges of building history-making companies."

The host provides context about HubSpot as "one of the few public tech companies pulling off over $2 and a half billion dollars of revenue and growing over 20%." He also explains Yamini's journey to becoming CEO, having joined HubSpot as the chief customer officer in 2020.

"Yamini joined HubSpot as the chief customer officer in 2020 and their CEO Brian Hallagan in 2021 had a tragic snowmobiling accident that thrust Yamini into the CEO position first in an interim role and then full-time 6 months after."

Timestamp: [01:03-01:41]

The conversation begins casually with Jubin reflecting on his recent interviews with former salespeople who have reached executive positions, connecting Yamini to this trend.

"I was just thinking when I was making my coffee I'm kind of on a hot streak with former salespeople that have gone into into the upper echelons of the professional world."

Yamini confirms her sales background, and the host mentions other successful executives like Carl, whom Yamini knows from her time at Dropbox when Carl was at Seoa serving as an advisor.

"I was at Dropbox when Carl was at Seoa and he was an adviser and I think I took most of his time. I'd be like 'How many times a week can I talk to you?' And he was like 'Well I don't know.' So I learned so much from him there."

The conversation turns personal as they discuss Yamini's name and origins.

"I'm originally from India... south India... and the name is like I don't I think it's half Sanskrit half Tamil."

Yamini notes the uniqueness of her name, mentioning that despite India's billion-plus population, she has never met another Yamini face-to-face, though she has heard of others with the same name.

Timestamp: [01:41-03:14]

Yamini discusses how she maintains connections to her Indian heritage, particularly through trips with her teenage sons.

"I mean maybe once every couple of years. I now have teen boys and the only way to get them to understand where we came from and have a sense of grounding in the world is to take them back and make them experience what I experienced."

She explains the challenge of helping her American-raised children understand her different upbringing and background.

"It's always tough because they can't relate. They've only seen everything here and then I'm like you know what you've got it good. They don't get what that is until I take them there and then we go visit where we are from."

Yamini mentions that her husband is also from India, and they go back together to visit their origins. She shares that she has two sons, ages 18 and 16, with the older one heading to college.

Timestamp: [03:14-03:59]

When asked about her financial background growing up in India, Yamini reveals her modest upbringing.

"Not at all, not at all. Our home that we spent most of our childhood in was about 350 square foot."

With a touch of humor, she recalls how the small space felt sufficient at the time.

"It was a mansion... I mean, it felt like a mansion. You know, I now I can go backwards and look at that and say 'Oh that was pretty modest.'"

Yamini describes her family as "squarely middle class," with her father running a small business "month to month, year to year" while her mother was a stay-at-home mom. She emphasizes how her parents "did everything possible" for her and her sister, and they "had no desires beyond what we got."

She shares a vivid memory of how she and her sister, who is two years older, would compete for limited resources in their small home.

"We would spend a lot of time like figuring out who gets the one desk in the house and we would have to like do things special to have the desk. The other one was sitting at the dining table and we would have to be like running around."

Timestamp: [03:59-05:07]

The conversation shifts to Yamini's current role, with Jubin asking about the scale of HubSpot today.

Yamini provides key metrics about the company, stating it has "9,000 people" and "three billion-ish" in revenue. When Jubin asks about the market cap, Yamini hesitates to check the current day's figure.

"Today might not be a good day to check. Today is not a good day to check."

Jubin mentions the figure from his notes: "30 billion," which Yamini confirms.

The host then raises an interesting question about the public nature of executive compensation and how Yamini's children might be aware of her high income, asking if this creates any discomfort given her humble origins.

"Your comp is like online. Like everybody like they can look it up. Your boys can look up like how much you make. Like it's all there right?"

Yamini acknowledges this reality with a simple, "And they do."

Timestamp: [05:07-06:02]

Yamini reflects deeply on her concerns about raising children in affluence when her own drive came from humble beginnings.

"What I worry about the most for my kids is that I grew up in this super small town in a super small house with not a lot and that honestly was the fire in my belly."

She describes how her mother instilled strong values and high expectations in her and her sister.

"My mom always thought that both of us... had to get great education, we had to be economically independent, we had to like do great things in our life and she always talked about that when we were growing up."

Yamini recalls how dinner conversations would center around trailblazers and achievers.

"Dinner tables would be the first lawyer in India, the first woman lawyer in India to win a big case... the first engineer to do something really cool, this doctor who would do something amazing, a mountaineer who did this, a pilot who did this."

Her mother's focus was particularly on female achievement, creating an inspired childhood.

"It was always like look what women can do and you know I know you're growing up here but nothing should stop you. So it was this very inspired childhood that I had."

This upbringing created challenges when Yamini reached college, as her engineering aspirations clashed with societal expectations for women in the 1970s and 80s.

"When I got to college I was like nobody was willing to take an engineer growing up... there was just a lot of like 'why are you here, you should be doing some arts and science'... So there was a dissonance between how my mom had raised us and what the conventional choices for women growing up in the 70s-80s looked like."

Timestamp: [06:02-08:01]

Yamini emphasizes that despite her achievement-oriented upbringing, money was never the primary focus.

"It was always achievement-oriented, never monetarily like the most important thing. For me, I never grew up thinking... I always grew up thinking I had everything I wanted even in my beautifully large 350 foot apartment. So it was never about 'oh I need to make more money' or 'I'm doing this for money.'"

She shares how she tries to instill similar values in her own children by taking them to an orphanage in India that she sponsors.

"In the place that I grew up we have an orphanage that we sponsor and there are about like 100 kids and you know we help them get an education and I make them go and spend days there."

Yamini explains the purpose behind these visits.

"It actually gives them a sense of look where you are and what your responsibility is in society is not just for you to make money and live in the Bay Area. It is to figure out how you can actually have a broader impact for people that don't have it."

When Jubin asks if her sons are aware of her wealth, she acknowledges they are but maintains firm boundaries about expectations.

"They do Google me and we have the conversation and the conversation I have with my boys is if you like this, work hard to get it because none of this is coming to you."

Yamini shares an example of how her sons might approach her about her income.

"They're like 'Mom, you made 25 million last year. How about like a car?' No. I mean, I've said that we will give them a good education."

She emphasizes her philosophy on raising children with drive and purpose.

"They're very clear that if they like the lifestyle that they have right now, they're going to have to earn the lifestyle that they have right now... There has to be some fire in the belly. There has to be a reason for you to do what you want to do and it has to come from within. It cannot just be given to you."

Yamini concludes by stating her and her husband's parenting goal.

"It's really important for me and my husband to raise our kids with a desire to have an impact in life, not just expect a lifestyle that they now enjoy."

Timestamp: [08:01-10:00]

• Yamini Rangan transitioned from Chief Customer Officer to CEO of HubSpot following Brian Hallagan's accident in 2021
• HubSpot has grown to 9,000 employees, approximately $3 billion in revenue, and a market cap of around $30 billion
• Yamini grew up in a modest 350-square-foot home in south India, which she credits as the source of her drive and ambition
• Her mother instilled achievement-oriented values, particularly emphasizing female accomplishment and economic independence
• Despite her current success and wealth, Yamini maintains that money was never her primary motivation
• She actively works to instill similar values in her teenage sons by taking them to India and having them spend time at an orphanage she sponsors
• Yamini is deliberate about not passing wealth directly to her children, believing they should earn their own success
• She prioritizes raising children who desire to make an impact rather than simply enjoying privilege

Timestamp: [01:03-10:00]

Companies:

• HubSpot - Yamini's current company, a public tech company with $2.5B+ revenue growing at 20%+
• Dropbox - Where Yamini previously worked
• Seoa - Company where Carl worked as an advisor to Yamini
• Kleiner Perkins - Venture capital firm where the host Jubin is a partner

People:

• Yamini Rangan - Current CEO of HubSpot, former Chief Customer Officer
• Brian Hallagan - Former HubSpot CEO who had a snowmobiling accident in 2021
• Carl - Mentioned as an advisor who influenced Yamini during her time at Dropbox
• Jubin - Host of the podcast, partner at Kleiner Perkins

Concepts:

• Fire in the belly - Yamini's phrase for the inner drive that comes from humble beginnings
• Achievement-oriented upbringing - The value system Yamini's mother instilled, focusing on accomplishment rather than wealth

Timestamp: [01:03-10:00]

The conversation begins with a discussion about the challenge of creating meaningful constraints for children who grow up in privilege, contrasting with Yamini's own naturally constrained upbringing.

Jubin points out the fundamental difference in their situations:

"Your constraints were not imposed, like that's just how your world was, whereas your kids' constraints are basically like you creating these constraints."

He questions whether artificially created constraints can truly instill the same drive that comes from genuine need:

"At the end of the day they still probably live in a nice house that they grew up in with you... I don't know, does that work? Does creating somewhat of false constraints actually like... is what keeps you up? That maybe or maybe not that creates the fire in their belly?"

Yamini acknowledges the uncertainty, given that her children are still teenagers.

"I don't know the answer. Look, my kids are teens... We'll have this conversation maybe like 5 years, 10 years and then I'll see if they really were able to accomplish something or put themselves in a path to accomplish something."

She shares that this concern has been on her mind since they were young:

"I used to worry a lot about this when they were young because we would travel on vacations and we'd go to nice restaurants. I'm like, where are they going to get it from?"

Timestamp: [10:06-11:08]

Yamini reveals that rather than just talking about values, she and her husband have found that modeling strong work ethics has naturally influenced their children.

"I work a lot and I enjoy working a lot. My husband works a lot. We've both been very career-focused and we've both worked a lot. And surprisingly, I've just seen that that has a huge impact in terms of the kind of work ethic and values that your kids get."

She proudly shares evidence that this approach may be working with her older son:

"My 18-year-old, he's a senior right now going off to college. I'll tell you the last two years he's worked harder than me and I was proud of that. And I saw him like grind it out a lot more than me and I was like, okay, maybe some of this is rubbing off."

Yamini emphasizes the difference between teaching values explicitly versus embodying them:

"You can teach values or you can live values, and I think we've tried to like live values and we're hoping that it kind of rubs off on them and they just take it forward in their life."

She believes in the power of consistent demonstration rather than lectures:

"It's a lot of conversations and it's a lot of like living what you want your kids to kind of take when they're adults."

Timestamp: [11:08-12:23]

Jubin asks Yamini to define what "working a lot" actually means in her life, seeking to understand her specific routine.

"What does hard work look like? Like, let's just take last weekend, were you working?"

Yamini reveals the consistency of her work ethic:

"Every weekend. There's not been a weekend that I've not worked in maybe 15 years."

She then describes her typical schedule during the workweek:

"During the work week, I start probably around 6, 6:30, and my first call is at 7, and then it's like a full day, lots of calls like everybody else. And then I'll have dinner with the kids and then I'll work till 11:00. That's my schedule. Any day is like maybe 12, 14, 15 hours."

However, Yamini explains that she's developed a critical boundary to maintain balance:

"Friday night when I'm done, whenever I'm done, it might be 8, 9, 10, whatever time I'm done on Friday, I don't touch my computer and I don't think about work till Sunday morning. I've constrained myself on that to say I need a break. It's almost like peak performance requires peak rest."

When Jubin asks if she still receives work-related communications on Saturdays, she reveals her firm boundaries:

"I've said to people that I will not respond on Saturday, so everybody in the company knows, all 9,000 people."

Even with board members reaching out, Yamini maintains her boundary:

"I might get like some board members... I'm not responding to them. I don't respond on Saturdays."

Timestamp: [12:23-14:25]

Yamini reveals that while she preserves Saturdays for rest, Sundays are dedicated workdays that follow a specific purpose and rhythm.

"Sunday morning, it's a full work day for me and it's my work day. It's like this is the time I read, this is the time I do deep thinking, this is the time I write, and it's a full day."

She explains her approach to communication on Sundays:

"I don't send out emails. My team knows that most of the time, almost always, I will schedule it for Monday morning. So they're probably waiting for this 5:00 a.m Monday morning emails, string of emails from me. But I work on Sundays and I think on Sundays and I do everything and then I send it out."

Jubin shares that he follows a similar Sunday routine and explains an unexpected benefit:

"I don't even know what Sunday scaries are anymore because I feel like I have so much control over the coming week... I feel like I'm capturing control in that Sunday."

Yamini enthusiastically agrees:

"I enjoy Sundays. I'm not scared of Sundays. I enjoy it because it's my time. I get to decide what I'm learning, what I'm doing, what I'm thinking, what I'm writing. It is completely my schedule. I have nothing else to disturb me except my own thoughts."

She expresses genuine excitement about the tech industry and how her Sundays allow her to explore and learn:

"This is such an exciting industry. Tech industry has always been exciting, but right now it is so exciting. There's so much to learn."

Yamini shares a recent example of how she spent a Sunday:

"Last weekend I had Loveble up and I was trying to create an app, and I did. I used to code way back and then I went into go-to-market and sales, so I've literally not coded in 20 years. And I was there on Loveble creating an app and feeling so powerful and vibing with it."

She concludes by describing her Sunday as a form of play:

"It's fun. That's my play day, it's like so fun."

Timestamp: [14:25-16:40]

Jubin shifts the conversation to explore Yamini's early days at HubSpot, which coincided with the beginning of the COVID-19 pandemic.

Yamini confirms she joined HubSpot in January 2020 as Chief Customer Officer, overseeing "marketing, sales, customer success, and operations" – essentially all go-to-market functions. This was just before COVID-19 became widely known.

She recalls how her onboarding plan was completely upended by the pandemic:

"Brian Halligan, our co-founder and at that time CEO, he was like, 'Ease yourself in for 90 days. I want you to do nothing. I want you to go and talk to people, talk to customers, talk to partners, talk to employees, and kind of form your own opinion.'"

However, the situation changed dramatically in March 2020:

"March was when borders started shutting down and people were asked to go back into their homes. And in one week, we saw churn grow like 200%. We had massive churn in the first couple of weeks of the month."

Facing this crisis, the original onboarding plan was scrapped:

"Brian was like, 'Forget what I told you. I need a plan in 5 days and we're going to go to the board and we're going to present what the plan is in 5 days.'"

Yamini describes the bold plan they developed:

"The plan that we presented to the board five days of brainstorming later was: we're going to cut the price of our starter tier by more than 75%, we're going to take a lot of paid features and move it to our free features, and we're going to create a pool of nearly $20 million as a customer relief fund."

She recalls the board's skeptical reaction:

"The board looked at us and said, 'What is that plan?' And we said, 'Look, customers are churning. They're all going to go bust unless they figure out how to do digital marketing.'"

Yamini explained their reasoning, focused on their small business customers:

"These are small businesses that were getting locked down completely. And if they don't get to figure out how to market digitally, and if they don't get to figure out how they drive sales digitally, they will go out of business."

When pressed about when they'd recover the $20 million relief fund investment, Yamini remembers her candid response:

"I looked at them and I was like, 'I don't know. It might take six months, it might take nine months, it might be never. And I say it out of deep conviction, not because I'm being crazy here, but I'm saying it out of deep conviction that if we can do the right thing for the customer and in this moment of sheer panic we can help them, then we earn their right to serve them and we can grow.'"

Timestamp: [16:40-20:42]

Yamini describes how HubSpot's bold customer-first strategy during the early pandemic ultimately led to explosive business growth.

"June came along and then everybody wanted to figure out how to drive digital marketing, how to drive digital sales. And that year in 2020 we grew the fastest. In 2021, our growth rate internally with the net new AR was something like 85%."

Jubin expresses amazement at this growth rate:

"That was on like a billion dollar base."

Yamini confirms:

"On a billion dollar base."

She reflects on the unexpected nature of this growth:

"Looking back, we can say okay, there was a lot of pull through and people bought a lot."

However, Yamini also acknowledges the operational challenges that came with such rapid expansion:

"Growth at that scale can be a challenge. We were not ready in terms of our infrastructure. We were not ready in terms of who we hired, how we onboarded them, how we made them successful. It was like, grow because this is what customers need."

She concludes by noting the dramatic shift in their strategy, from initially preparing for contraction to suddenly managing hypergrowth:

"That is absolutely insane because you whiplashed first towards contracting."

Timestamp: [20:42-21:40]

• Creating artificial constraints for privileged children may not easily replicate the natural "fire in the belly" that comes from genuine need
• Modeling strong work ethics and values can be more effective than explicitly teaching them to children
• Yamini maintains a rigorous work schedule (12-15 hours on weekdays) but strictly protects Saturdays as a non-work day
• Sundays serve as dedicated deep thinking and preparation days, providing a sense of control over the upcoming week
• When COVID hit, HubSpot made a counter-intuitive decision to cut prices by 75% and create a $20M customer relief fund
• Despite initial board skepticism, the customer-first approach during crisis led to unprecedented growth – 85% growth on a $1B revenue base
• Rapid growth created significant operational challenges as the company wasn't prepared for such sudden expansion
• HubSpot experienced a dramatic strategic "whiplash" – initially preparing for contraction before pivoting to manage hypergrowth

Timestamp: [10:06-21:40]

Companies:

• HubSpot - Where Yamini serves as CEO, experienced 85% growth during pandemic
• Loveble - App development platform Yamini used to create an app on her weekend

People:

• Brian Halligan - HubSpot co-founder and CEO when Yamini joined in January 2020

Concepts:

• Customer Relief Fund - $20 million fund HubSpot created to help customers during pandemic
• Peak performance requires peak rest - Yamini's philosophy on balancing intense work with necessary recovery
• Net new AR - Annual recurring revenue metric mentioned in context of HubSpot's 85% growth
• Sunday strategy - Approach of using Sundays for deep thinking and preparation for the week
• Living values vs. teaching values - Yamini's parenting philosophy of modeling behavior rather than lecturing

Timestamp: [10:06-21:40]

The conversation begins with reflections on the pandemic-era business mindset that pervaded the tech industry during HubSpot's explosive growth period.

Jubin characterizes the progression they experienced:

"For a few months of like a hard contraction, the bottom was falling out with churn, then you basically go on a year and a half run of demand in the next 5 to 10 years getting pulled forward to this present 18 months."

He describes how companies responded to this unprecedented demand:

"Then in order to meet that demand, you and basically every other tech company was like, 'Well, I think this is how the future is going to be forever.' Like, people are going to be digital, people are going to be remote, we're just pulling the inevitable forward and this is our new normal. That was kind of like the ethos of the time."

Yamini acknowledges this characterization while admitting there were signs this wasn't sustainable:

"I think that was the ethos, although you kind of knew that it was not sustainable. The kind of growth that we were seeing... but like Zoom, what was happening with Zoom was like even crazier. We would look at our whatever 80-ish% growth rate and they were growing like 350, and we were like, 'Oh my god, that is crazy.' And we know that was not sustainable."

She confirms the prevailing business imperative of that moment:

"But that was the absolute ethos. It is: we have to grow, we have to serve, we have to make sure that we can keep up with the demand at that time."

Timestamp: [21:46-22:52]

Jubin questions the now-common narrative that pandemic-era growth was "irresponsible," pointing out the practical challenges companies faced.

"I hear a lot of founders and CEOs now say, 'Oh, I kind of grew irresponsibly through that period.' But my question is, if you're growing at 85% on a billion dollar base and you have all of this demand, how do you... you have to hire people and you have to hire people really quickly and you have to do it remote."

He highlights the inevitable trade-offs:

"So you're going to lower the bar because there's no other choice. Like I don't know what gives there."

Yamini pushes back against the revisionist perspective:

"I think you can always look back at events and have a level of clairvoyance that you didn't have at that point. So I don't believe in saying, 'Oh, we grew irresponsibly.' We had demand and our job was to make sure that we were helping our customers through a very important digital transformation, and we did it."

She acknowledges specific challenges they faced:

"Now I would say that there were parts of our infrastructure in terms of the data, in terms of the systems, in terms of processes - we were totally not ready for that type of growth."

Yamini also reflects on the competitive hiring environment:

"The ethos of that time was that the Metas and the Googles were giving out these big comp packages and they were hiring, and we were like, 'Okay, we got to compete and we have to continue to hire.'"

She maintains that their growth wasn't irresponsible but contextual:

"I think it was not irresponsible. It was the 'how' we met that moment in time and how we were trying to do it."

Timestamp: [22:52-24:07]

Yamini explains the challenges that emerged as the pandemic-era boom subsided and how the company had to adjust.

"Now we've learned a lot. I think we've had to put the foundations back again."

She highlights a specific skills mismatch in their pandemic hiring:

"We learned that some of the folks during that time were really good at order taking, but then when the tides turned and we had to get them to fish, they didn't have the skill set. We didn't hire them for that skill set."

This realization forced difficult personnel decisions:

"So we had to retrain them or actually let go of them and hire a whole new set of folks."

Yamini summarizes the challenging transition period:

"It's all been hard. It's all been hard."

Timestamp: [24:07-24:47]

Jubin draws a thought-provoking parallel between the pandemic growth ethos and the current AI frenzy.

"The general ethos now in March of 25 is everyone's building out some version of a tuned frontier model that they're taking off the shelf from Anthropic or OpenAI. They're hiring a bunch of expensive AI engineers that everybody is continuing to compete for. Everyone is throwing a bunch of compute at a problem. Everyone says that we don't have enough data, our data is not in order."

He wonders if this is simply history repeating itself:

"I'm just hearing you say these things and I'm like, 'Oh this is the current thing.' Like this is just a different name to the current thing."

Yamini acknowledges the similarity while asserting this technological shift is more fundamentally transformative:

"I think you are right. It seems different. For the better part of the last decade everybody was like, 'What's the next thing? What's the next thing? Maybe it's web three, maybe it's something else.' And we were all kind of looking for what is the next thing after SaaS."

She argues for AI's distinctive impact:

"I do think that minus the hype, minus all the hot takes about AI, it is a truly transformative technology, not because of how cool it is, but because I think it fundamentally reshapes the kind of work that we can now do."

Timestamp: [24:47-25:58]

Yamini provides a vivid historical perspective on how CRM systems have evolved, using it to illustrate why the current AI shift is genuinely transformative.

She begins by recalling the original CRM experience:

"When I started at Siebel, that was the original CRM company in sales, the first thing was like, 'Here's a target account selling methodology and then you have a CRM system that is your rolodex.'"

Yamini describes the labor-intensive process that defined early CRM usage:

"When you meet someone, you meet like five people during the day, you go in there and you enter your contacts of who you met. Then you're putting in notes of what conversations you had with them, and then you are trying to send an email to all of them to make sure that you're developing those relationships."

She emphasizes the fundamental purpose of these systems:

"That was the CRM. The CRM was for a seller to do tasks in order for them to drive a level of productivity, and that's what we grew up in."

Yamini then contrasts this with the AI-powered CRM experience emerging today:

"Now you look at AI, what you can do today is you can listen to this conversation. AI can listen to this conversation, say 'Yamini is talking to Jubin, Jubin is not in her contact base' and this is the conversation that they had and this is the follow-up they should have."

She outlines the automated workflow this enables:

"And when I go back it can say, 'Do you want me to add Jubin to your contacts?' Yes. 'Do you agree that this is the summary of your conversation?' Yes. 'Do you want to send this follow-up?' Yes. Okay, it's done."

Timestamp: [25:58-27:16]

Yamini articulates why AI represents a fundamental paradigm shift in how technology supports human work, distinguishing it from previous tech trends.

"That is what is exciting. The jobs that we all did as a marketeer, as a salesperson, as a support person is now completely getting rewritten and we can do more. That is what is so exciting about this."

She acknowledges certain similarities to past tech cycles while emphasizing the deeper impact:

"While there are some parallels in terms of the ethos of like how crazy people are growing and all the conversations that are happening, this is fundamentally exciting because you can do better things with your time."

Yamini highlights the transformative potential:

"You can re-imagine amount of work that can be done and it is no longer about software helping you do tasks, it is about software doing tasks to help you that then maximizes the results and the outcomes that you can achieve in the time that you spend."

Jubin strongly agrees, sharing his own experience:

"When I was starting out in my career, I was probably making 100 cold calls a day and writing literally 4 to 500 emails a day and copy and pasting them."

He mentions a company in his portfolio addressing this inefficiency:

"We're investors in a company called Nooks. It's just going to do it all, right? It just does it all. It literally just does all of that work."

Jubin reflects on the wasted effort:

"I didn't need to be doing that work. What a waste of time. I still needed a job to do. There was a job for me to be done there, but it was not that job."

Timestamp: [27:16-28:35]

Yamini expands on Jubin's point, articulating how AI can free salespeople to focus on their true value-add rather than administrative tasks.

"The job to be done for you as that sales rep, and this is how I started my career as well, is to close deals and is to win business. Is to be in front of customers, is to understand your customer's pain point and to win them as a customer. That was the job to be done."

She describes the extensive preparatory work that traditionally consumed salespeople's time:

"In order to do that job, you researched companies, you cold called, you wrote a bunch of emails, you followed everything up, and then you did all of that to get a sliver of time in front of the customer. And that was the paradigm then."

Yamini shares a striking statistic from her years in the industry:

"The really incredible statistic for 20 years I've been tracking this: what's the time a salesperson spends in front of a customer? And this has not moved. It's like 25%. And if you got your act together and you have great operations, you have amazing data, you have great systems, it's 27%."

She highlights the minimal improvement despite massive investments in sales technology:

"So you literally have like a 2% improvement if you get everything right in terms of the time in front of customer. And everything else is the prep that you're talking about. It's the research."

Yamini recalls her own experience managing sales teams:

"When I first moved on to operations, I would literally beg the sales team to be like, 'Can you please complete your notes in the system because the next person and the next person needs a better handoff.'"

She concludes with optimism about the current transformation:

"So that is changing and it's so cool. It's so exciting to see what companies are doing. HubSpot is completely there and that's what we're trying to imagine for our customers."

Timestamp: [28:35-30:13]

• The pandemic created a "pulled-forward" growth environment where companies experienced years of digital adoption compressed into months
• While many now characterize pandemic-era growth as "irresponsible," Yamini believes they were appropriately responding to customer needs during digital transformation
• Companies faced significant infrastructure and hiring challenges during hypergrowth, including hiring people with "order-taking" rather than "fishing" skills
• Today's AI boom has parallels to the pandemic tech boom in terms of investment patterns and competitive dynamics
• Unlike previous tech cycles, AI represents a fundamental shift from "software helping you do tasks" to "software doing tasks to help you"
• CRM systems have evolved from being record-keeping tools where users input data to intelligent systems that can capture, process and act on information automatically
• Despite decades of sales technology development, the percentage of time salespeople spend with customers has remained stubbornly at 25-27%
• AI promises to dramatically increase this customer-facing time by automating the administrative burden of sales roles

Timestamp: [21:46-30:13]

Companies:

• HubSpot - Yamini's company, experiencing hypergrowth during pandemic and now embracing AI transformation
• Zoom - Mentioned for its extraordinary 350% growth rate during pandemic, compared to HubSpot's 80-85%
• Meta - Referenced as setting competitive compensation packages during pandemic hiring spree
• Google - Referenced alongside Meta for aggressive pandemic-era hiring and compensation
• Anthropic - AI company mentioned as source of frontier models businesses are building upon
• OpenAI - AI company mentioned as source of frontier models businesses are building upon
• Siebel - Described as "the original CRM company" where Yamini worked early in her career
• Nooks - Company in Jubin's investment portfolio automating sales outreach tasks

Concepts:

• Pandemic ethos - The belief during COVID that digital/remote trends represented a permanent, accelerated shift
• Order taking vs. fishing - Metaphor for different sales skills: passively processing incoming demand versus actively creating opportunities
• Target account selling methodology - Traditional sales approach mentioned from early CRM days
• Software helping you do tasks vs. software doing tasks to help you - Yamini's distinction between traditional software and AI
• The 25% statistic - The persistent finding that salespeople spend only about a quarter of their time in front of customers
• SaaS to AI transition - The industry shift from Software-as-a-Service to AI-powered platforms

Timestamp: [21:46-30:13]

The conversation begins with a discussion about the difficult strategic decisions companies face when determining how aggressively to invest in emerging technology trends.

Jubin highlights the high-stakes dilemma executives faced during the pandemic:

"In the days of everyone being remote and it's going to last forever and this digital demand is going to sustain for decades to come, the problem is - which is similar to now - whether it's true or false, if you're wrong... if it's true and you're wrong and you didn't make the right investments at that point, you're screwed."

He elaborates with a concrete example:

"Meaning like if you're growing 100% at a billion dollar base and you're just like, 'Oh no this isn't going to last,' and it does last, you just left hundreds of millions of dollars on the table."

Yamini emphatically agrees:

"Exactly, exactly right."

Jubin then draws a parallel to current AI investments by major tech companies:

"These big tech companies now like Meta and Google and Microsoft, the investments that they're making in infrastructure are insane, like insane. It's insane like we've never seen dollars spent like this."

He points out the potential downside of not investing:

"But like what are they going to do? Like what if they're wrong? What if this is maybe not even enough investment? And Microsoft decided not to do it and Meta and Amazon did - like they missed the whole thing."

Yamini reiterates:

"Absolutely, absolutely."

Timestamp: [30:21-31:31]

Yamini articulates her philosophy for navigating technology hype cycles by anchoring decisions in customer value rather than technological trends.

"This is why it's so hard. I think one of the things I feel is there's a lot of hot takes and hype and all of these, and every cycle whether it turns out to be real or not has hot takes. Every day like some crypto this and web 3 that and now AI this."

She emphasizes the fundamental business principle that guides her approach:

"It really comes down to customer value and you got to go back to - it doesn't matter what all this technology talk does. You got to go back to who's your customer, what is their job to be done, and can you improve that and add value."

Yamini shares HubSpot's guiding principle:

"That's how we look at it. We have a North Star which is 'solve for the customer' - SFTC. We talk about this all the time."

She explains how this principle filters technology decisions:

"It comes back to: forget all the hype and forget all the cool technology - can we take a neat feature of AI and make it a necessary feature in AI? If we can prove to ourselves with customer usage and repeat value that we deliver, then there's something in the cycle."

Yamini contrasts this with technology that lacks staying power:

"If it's the cool thing that you do today and then next week it's churned and everybody is left, then there is no value."

She acknowledges the uncertainty inherent in early technology adoption:

"At the beginning of the cycle, you just have to use some kind of pattern recognition to say, 'Is this going to work or not?' and make a bet. And you cannot be wrong, and that's what happens."

Timestamp: [31:31-33:01]

Yamini draws parallels to previous technology transitions, particularly the shift from on-premise software to cloud computing, highlighting how established companies often struggle with disruption.

"I used to work at SAP, and back in those days there was a lot of question of, 'Is cloud real? Will on-premise ever go away? Is cloud real? Would CIOs ever trust data that's not in their data center and is in some kind of public cloud?' These were real debates."

She contrasts this historical skepticism with today's AI adoption:

"Now it's not the same thing. I think all of us who've been established for a while, or if it's a startup, we know and see the value of AI. And we're kind of really focused on what is that value for customers."

Jubin suggests that SAP's fate could have been different:

"If Siebel had had deep belief and conviction that SaaS was actually going to be the thing that ultimately upended their business and enabled Salesforce to become a big company, they probably would have done that."

Yamini agrees:

"They just didn't."

Jubin concludes:

"And then they got cannibalized."

He then predicts a similar fate for current SaaS companies that don't adapt:

"I think that's about to happen all over again to many of these SaaS companies... if you're one of these traditional SaaS companies - traditional as in like you were born in the last 20 years - and you're not leveraging this technology, you're probably going to die. You're probably going to get completely upended."

Timestamp: [33:01-34:15]

Yamini challenges the traditional disruption narrative, suggesting that AI represents a market expansion rather than just a replacement of existing technologies.

She first acknowledges the lessons of past disruptions:

"Everybody, every one of us running tech companies now, we've got the memo. We read Innovator's Dilemma. We looked at Blockbuster, we looked at BlackBerry, we lived through Siebel, we lived through all of this. We've got the memo, and there is no hesitation in looking at what is happening within the tech industry to say this is big, we're going."

Yamini then reframes the conversation about AI disruption:

"I think about this disruption conversation slightly differently. If you think about the way to define disruption, it's that you have a certain market, there is a new startup that comes into that market, and they eat your TAM and they reset your ability to grow. That is the disruption."

She contrasts this with what she sees happening with AI:

"I think what is happening right now is that there is a software market, but that market actually now got 10x bigger because it's now software and work market."

Yamini elaborates on this expansion:

"What you talked about, paralegal, is work. Typically, software never did that, and it might have provided some help, but it didn't actually translate work. So the overall addressable market went from software to software plus labor, which is 10 times bigger."

She explains why this shifts the strategic focus:

"Which means your job is not sitting there thinking about disruption and 'Is my market going to get smaller?' Your job is to define what you are going to do to get a bigger percentage of this 10x market."

Jubin agrees:

"That's right."

Yamini concludes with optimism about incumbent companies:

"That is different, and I think that's why the incumbents or the ones that have been around, they're moving faster and they are redefining what this looks like within the market. And it's exciting."

Timestamp: [34:15-36:05]

• Companies face a high-stakes dilemma when deciding how aggressively to invest in emerging technology trends - under-investment risks missing massive opportunities
• Major tech companies like Meta, Google, and Microsoft are making unprecedented infrastructure investments for AI, recognizing the existential risk of being left behind
• Amid technology hype cycles, customer value should remain the North Star - successful innovations must transform from "neat features" to "necessary features"
• HubSpot uses "Solve for the Customer" (SFTC) as their guiding principle for navigating technology decisions
• Historical parallels exist between AI adoption today and cloud computing adoption in the past, when established companies like SAP questioned whether cloud would replace on-premise software
• Companies that failed to embrace previous technological shifts (like Siebel with SaaS) were ultimately cannibalized by more adaptive competitors
• Current SaaS companies that don't effectively leverage AI technology face similar existential threats
• Unlike traditional disruption where startups eat into existing markets, AI represents a 10x expansion of the addressable market by combining software with labor
• This expansion shifts the strategic focus from defending against disruption to capturing a portion of a much larger market
• Established companies that understand this dynamic are moving quickly to redefine their offerings within this expanded market

Timestamp: [30:21-36:05]

Companies:

• Meta - Mentioned for making massive AI infrastructure investments
• Google - Referenced alongside Meta for unprecedented AI spending
• Microsoft - Cited as making massive AI infrastructure investments
• Amazon - Mentioned in the context of AI investment strategy
• SAP - Where Yamini previously worked, used as example of company that questioned cloud adoption
• Siebel - Referenced as example of company that failed to adapt to SaaS, enabling Salesforce's rise
• Salesforce - Mentioned as the company that disrupted Siebel by embracing SaaS
• HubSpot - Yamini's company, which uses "Solve for the Customer" as its North Star
• Blockbuster - Cited as classic example of disruption that current tech executives have studied
• BlackBerry - Mentioned alongside Blockbuster as cautionary tale of disruption

Concepts:

• SFTC (Solve for the Customer) - HubSpot's guiding principle for evaluating technology
• Innovator's Dilemma - Book by Clayton Christensen about disruptive innovation, mentioned as required reading for tech executives
• TAM (Total Addressable Market) - Referenced in discussion of how AI expands rather than cannibalizes existing markets
• Neat vs. necessary features - Yamini's distinction between flashy AI capabilities versus those that deliver lasting customer value
• Software plus labor market - Yamini's concept of how AI expands the addressable market by 10x by taking over work previously done by humans
• Hot takes - Referenced multiple times as the excessive hype that surrounds technology cycles (crypto, web3, AI)
• Cloud computing transition - Used as historical parallel to current AI transition

Timestamp: [30:21-36:05]

The conversation begins with a frank discussion about AI's impact on labor, particularly in customer support roles.

Jubin states directly:

"You are 100% not going to need as many customer support people. That's the truth. You are going to replace or not hire future customer support people that you otherwise would."

He emphasizes the financial implications:

"Those are whatever salary they are. You're just getting rid of those salaries or reallocating what you would be otherwise hiring in those salaries towards something else."

Yamini confirms:

"Yep, at like a 20 to 50% clip or more."

Jubin notes how this fundamentally changes business models:

"That's very different than charging a license or a seat-based fee for some service that you're offering."

Yamini agrees:

"Absolutely."

Timestamp: [36:10-36:47]

Jubin explores how data advantages create defensibility for incumbents in different markets, using specific examples.

"The incumbent question is one that I'm really fascinated by because we don't want to go up against, ideally, a non-tech-savvy incumbent that we are cannibalizing, not necessarily HubSpot."

He illustrates with a concrete example:

"I'll give you an example that comes to mind right now. There's a company called Axon. You probably never heard of it. They're a $60 billion public company. They do tasers. They have a 99% market share of all tasers in the country."

Jubin explains Axon's evolution:

"Product number two was body cams for police officers. I think on Amazon or Microsoft's public cloud, they're larger than Netflix and Snapchat combined or something, with how much data they're sending to the public cloud, just to give you a sense of their scale."

He describes their AI initiative:

"What they're doing is they have built a co-pilot for police officers, because after a police officer does a traffic stop, they then have to go back to the office and transcribe all the things that happened. Now they can just dictate it as it's happening, and it automatically transcribes that in a way that's saving them literally hours a day."

This represents a significant efficiency gain:

"That's like half their job."

Jubin reflects on the competitive implications:

"Do we think we should make a bet in the police co-pilot? Probably not, in that respect, because they have all the data."

He contrasts this with other markets:

"For doctors, I think there's a pretty obvious use case there. There's maybe a difference here."

Timestamp: [36:47-38:35]

The conversation shifts to the complex question of data ownership in AI systems and how that impacts competitive advantages.

Jubin raises a provocative point:

"The weird thing is that the current state of the market is that we are paying rent for somebody else to use our data."

He uses a specific example to illustrate:

"Let's take Salesforce, right? That's not Salesforce's data. It's the customer's data."

Jubin contrasts this with Axon's situation:

"That's different than the police use case, do you know what I mean? I don't know how that unfolds."

He acknowledges Yamini's position:

"I think that they have a huge data advantage, but I think you have a huge data advantage. But like how you use that data and what tools can you offer, I don't know the answer to that. I just don't know how that's going to play out."

Yamini responds by articulating HubSpot's approach to data aggregation as a value proposition:

"I'll tell you the ability to bring together the data and give it to the customer who is responsible and who owns the data is actually valuable."

She elaborates with a concrete example:

"One of the reasons why customers like HubSpot is we help them get all their structured data about the company, the contact, the notes, all of that in one place, and it's super easy."

Yamini explains how AI expands this capability:

"Now we are bringing together all of this unstructured data - the conversations, the emails, the Slacks, the Zoom meetings, the phone calls you have, the transcripts from all of that - because AI can do more with that unstructured data."

She emphasizes their strategic positioning:

"We have a natural advantage of bringing the structured data, unstructured data, and even external data from 10Ks, 10Qs, transcripts, communities, any of that together to give that back to the customer. We don't even need it for training."

Yamini provides a specific use case:

"If we say 'hey, your salesperson is having this conversation' and if I look at the 10 unstructured conversations, these two are best in class, these other eight have to learn, so I can actually expose what the first, the top two reps are doing and make it better for the other reps. That's a value."

She summarizes the key advantage:

"The ability to bring data together to drive real-time insights from a larger volume of data to help customers get value is the advantage right now."

Timestamp: [38:35-41:52]

Jubin raises the critical challenge of attracting top AI talent when competing against exciting new startups.

"If you want to go build the products and services that you think your customers need in this new world, you're going to have to hire the best of the best."

He points out the competitive disadvantage established companies might face:

"Those best of the best often, they'll look at a company like Harvey and they'll be like, 'Wow that's the new shiny thing.' That's who you're competing against for that talent."

Jubin frames the strategic challenge:

"If talent is the enablement function to get you from where you are to where you want to go, that often, I imagine, is tricky."

Yamini acknowledges the challenge while explaining HubSpot's approach:

"I think it has always been tricky. The part of it is the risk profile of the person and what they're trying to learn."

She highlights HubSpot's structural advantage:

"In the case of HubSpot, we act like a startup within a startup. There are so many innovation bets and so many innovation teams."

Jubin interjects with recognition:

"Which you always have, by the way. Your history is there."

Yamini confirms their acceleration:

"We've put these bets and now we're actually accelerating the pace of that product and innovation bets that we're putting."

She describes their pitch to potential talent:

"A lot of times we'll have conversations like, 'Okay, you want to do something, why don't you do it here? And here's how we'll enable it. And by the way, we'll give you the resources and there's a higher chance of you being successful.'"

Yamini acknowledges different risk preferences:

"Ultimately it comes down to the risk profile of that individual. Of course they can go work for startups, knowing that not every one of these companies are going to become successful, or they can work in an innovation bet within a company like HubSpot."

She emphasizes the learning opportunity in the current moment:

"This is a period that we're all going to look back and say, 'Oh my god how much did we learn in that period?' There are points in times of my career where I'm like, 'Oh my god, maximum learning,' and that's what excites me, and that's right now."

Yamini shares how she frames this with her team:

"I tell our teams all the time, 'You're going to look back at these three years where I know we're working super hard and we're going even faster, but you're going to look back and say that is when I learned the most and that is when it was exciting.'"

Timestamp: [41:52-44:28]

Jubin asks Yamini about the emotional impact of leading through this period of intense competition and transformation.

"Does it keep you up at night? Everyone now sees basically every category up for grabs. The race is reset, and of course you're in one of the mothers of all markets."

He notes the intense competitive landscape:

"It is reset. There are like 20 companies, maybe 100, all looking at CRM."

Yamini responds with remarkable candor about her emotional state:

"I mean, it does. Jubin, I wake up excited and scared at the same time. It's like this... I'm like, 'Okay, today we feel really good and there's so much excitement.'"

She shares a recent experience that exemplifies this duality:

"Last week we had this whole thing where we brought the leadership team with our top GMs in product as well as engineers, and we had like two days of brainstorming. We had so many ideas and we're so excited, and then you look at some other tweet from someone else and you're like, 'Oh my god.'"

Yamini summarizes:

"So I think it's both."

She explains her approach to managing this uncertainty:

"You're going to have to really distill it down to what do you need to do now, what do you need to do in the next 3 months, and what's the hypothesis of the world that you have over the next year. Because I think anything over that period, who knows."

Yamini acknowledges the rapid pace of change:

"Three years, 5 years from now, if AG comes in, who knows what the world is going to look like? We can only plan for the next year in very, very short increments of time."

Timestamp: [44:28-45:47]

The conversation concludes with reflections on the unprecedented speed of change in the technology industry.

Jubin shares a personal anecdote:

"We run a group of CIOs here at Kleiner Perkins. There's about 30 of them and we met yesterday. I was putting together a deck to give a state of AI, state of the valley, all this stuff. I gave the same presentation two months ago. I basically had to redo the entire deck."

He emphasizes the rapid pace:

"Two months ago, I basically had to redo the entire deck."

Yamini responds positively:

"I believe. I was like, 'What is happening?' Exciting though. It's incredibly exciting."

Jubin references a historical perspective for context:

"John Chambers used to say that every 5 years he felt like he would have to reinvent himself as a company and reinvent Cisco. Reinvent Cisco and reinvent himself as a leader, every five years that was like about his clip, and he was like that was hard."

He contrasts this with today's reality:

"Right now these early stage startups are reinventing themselves literally every six months, every six months."

Yamini applies this to her own experience:

"We're a much bigger company. Every year I've been as a CEO, I've had to reinvent what I'm doing and my mental constructs. Every year there's something completely different that we are trying to drive at HubSpot."

She agrees with the accelerated timeframe:

"It's no longer 5 years, it's probably 6 months, maybe even 3 months. You're trying to run really, really fast."

Jubin adds additional layers of complexity facing Yamini's position:

"It's even crazier for you because you have all of these new people that are popping up trying to take your throne. You have these foundational models that are dropping 10x in price every year, 10x. And then they're improving, I don't know what, but like a lot, crazy fast every year. So it's like all of these things at once and you're like, 'Oh my gosh.'"

Yamini concludes with a simple assessment:

"It's insane. It's exciting."

Timestamp: [45:47-47:24]

• AI will significantly reduce customer support staffing needs by 20-50% or more, fundamentally changing the economic equation from seat-based fees to labor replacement
• Companies with proprietary data advantages (like Axon with police data) have strong defensive moats in specific verticals
• The complex question of data ownership creates tension in the AI ecosystem - customers own their data, but companies derive value from analyzing it
• HubSpot's strategy focuses on aggregating structured, unstructured, and external data to provide insights back to customers
• A key value proposition is identifying best practices (like top-performing sales conversations) and helping others replicate them
• Attracting top AI talent is a critical challenge when competing against exciting startups
• HubSpot counters this by creating "startup within a startup" environments and emphasizing the learning opportunity of this transformative period
• Leaders like Yamini experience the duality of being "excited and scared" during this period of intense change and competition
• Planning horizons have compressed dramatically - focus is now on 3-month increments rather than multi-year plans
• The pace of change has accelerated from reinvention every 5 years (John Chambers' era) to every 3-6 months today
• Multiple factors compound complexity: new competitors, rapidly improving models, and dramatically falling costs

Timestamp: [36:10-47:24]

Companies:

• HubSpot - Yamini's company, focused on aggregating data to provide customer insights
• Axon - $60B company with 99% market share in tasers, now building AI co-pilots for police officers
• Salesforce - Referenced in discussion about customer data ownership
• Harvey - Mentioned as an exciting AI startup that competes for talent
• Amazon - Mentioned regarding Axon's cloud usage
• Microsoft - Cited regarding Axon's cloud infrastructure
• Netflix - Used as comparison point for Axon's data scale
• Snapchat - Used as comparison point for Axon's data scale
• Cisco - Referenced through John Chambers' approach to reinvention
• Kleiner Perkins - Jubin's venture capital firm that runs a CIO group

Concepts:

• Co-pilot - AI assistant for specific roles (like police officers), automating documentation
• Structured vs. unstructured data - Distinction between traditional database information and conversational content
• 10Ks/10Qs - Financial reports that can provide external data for AI analysis
• 20-50% clip - The expected reduction in customer support staffing due to AI
• Startup within a startup - HubSpot's approach to innovation and talent attraction
• AG (Artificial General Intelligence) - Referenced regarding future uncertainty
• Risk profile - How individual talent evaluates opportunities at startups vs. established companies
• Foundational models - The base AI systems dropping in price by 10x annually
• The state of AI - Rapidly evolving landscape requiring frequent reassessment

People:

• John Chambers - Former Cisco CEO known for reinventing the company every 5 years

Timestamp: [36:10-47:24]

The conversation shifts to Yamini's unexpected journey to becoming CEO of HubSpot, beginning with Jubin asking about the timeline.

"At what point did you become the CEO? What point in time?"

Yamini reveals:

"March 2021."

She then begins to share the surprising story of her succession.

"So what happened was this. I join and first year we're running super hard. At the end of year one, Brian texts me."

Yamini clarifies who Brian is for context:

"Brian's the CEO... our co-founder and CEO for 15 years."

She recounts the unexpected message she received:

"He texts me on the eve of Christmas and he's like, 'Hey, you'll be my successor and you're a part of my succession plan.' And then I texted him back saying, 'Everything is going to be fine. You're going to be doing this for another 10 years.'"

Yamini explains that they had just one brief conversation about succession, and she didn't think much more about it until a sudden turn of events:

"Then March comes along and unfortunately Brian had a snowmobile accident and he broke a lot of bones. Thankfully he's now completely fine, but he needed to go and take care of himself."

Timestamp: [47:30-48:31]

Yamini describes the abrupt leadership transition that occurred following Brian's accident, highlighting the unexpected nature of her ascension to the role.

"He actually texts me again. He says, 'Remember I told you about this? If I ever get hit by a bus, you have to run it. I need you to run it.'"

The timing of this transition was particularly challenging:

"This was March 2021. This is like from the hospital sending you this, and this is like 15 months after I joined the company."

Yamini recalls their initial conversation about the temporary arrangement:

"We were like, 'Okay, you take the time,' because he needed to recover, he needed time for surgeries and all of that stuff. And we said, 'Okay, you can do that. We'll take care of it.'"

She emphasizes the challenging business context:

"This was March 2021. This was the time the company is growing like crazy and we're trying to grow fast enough to make sure that we are capturing all of the growth."

When Yamini asked for guidance, Brian's response was characteristically blunt:

"So what do you want me to do? And he said, 'You know, don't screw it up.' He actually said that. He did. He used a different word, but I won't say it."

Jubin asks for clarification about her initial role:

"Was it an interim CEO or was it the CEO?"

Yamini explains:

"That was an interim CEO because he was like, 'I'm coming back.' He was like, 'Well...' and you always thought Brian's going to be here forever, I think. So we didn't even have that conversation. He was like, 'Run it, don't mess it up, and keep going.'"

Timestamp: [48:31-49:46]

Yamini describes how what began as a temporary leadership assignment unexpectedly became permanent, showcasing the unpredictable nature of executive succession.

She initially assumed Brian would return to his role:

"I, for sure, thought that he was going to come back and run, and so I had this list of when Brian comes back, he needs to fix these things. And it was a very long list. In six months, it had grown to like multiple pages. I need to talk to him about this and this and this."

Yamini recounts the surprising moment when Brian returned:

"So he comes back, and by the way, he's completely fine now, but he comes back in like July or August, three, four months later. Four months, he was not fully recovered."

She describes her expectation versus the reality:

"We were thinking that he's going to be back in like 6 months, and he goes, 'No, you're doing it and keep doing it. Board and I think that you're doing a great job, and we want you to become the CEO.'"

The transition became official:

"So in August 2021, I moved from what I was doing as an interim CEO to kind of taking on the CEO."

Yamini emphasizes the challenging circumstances surrounding her permanent appointment:

"It was crazy times, right? Because that was the year we were growing like crazy. We'd done some of these transitions. It was tough for the leadership team to kind of take the company, make sure that we had this whole internal challenge of running the company when the founder was out taking care of himself. And then we had to make sure that we were making the right decisions to grow."

Timestamp: [49:46-50:54]

Jubin and Yamini discuss the tumultuous market conditions that followed her appointment as CEO, highlighting the challenges of leading through dramatic economic shifts.

Jubin observes:

"Then basically within a year from that point, interest rates go up and your growth rate gets cut in half. And you're like, 'Well, welcome to the show. Here we go.'"

Yamini points out the even shorter timeframe of stable conditions:

"It was not even that. October 2021 was the peak of the market, so I had like two months. October 2021 was the peak of the market, and then obviously things started going down."

She describes the rapid economic deterioration:

"By the time we came into 2022, April 2022, customers were clearly pulling back. High interest rates, high inflation."

Yamini offers her perspective on the macroeconomic factors:

"Now we can look back and say that combination of pumping a lot of money into the economy and letting the interest rates go flying and driving inflation was just not a good combination."

She details HubSpot's response to these changing conditions:

"The impact of it was by April 2022, we started seeing the pullback. And then we're like, 'Okay, turn the whole ship around. We got to slow down hiring, we got to slow down where we're going to grow, and we have to recalibrate all of the plans.'"

Yamini summarizes her experience:

"So yeah, it's been a roller coaster."

Timestamp: [50:54-52:04]

When asked about her emotional reaction to becoming CEO, Yamini shares a deeply personal reflection on her journey and how the reality exceeded even her imagination of what was possible.

Jubin asks:

"When you became CEO, how did you feel? Like, what did you actually think?"

Yamini responds with raw emotion:

"I think my life kind of flashed in front of me. And people say that, but look, I grew up in a super small town. When I was growing up, we didn't have a high school in my town, so my mom moved to a different city to get my high school education completed."

She describes her humble beginnings in the United States:

"Then I had this dream of coming to the US, and I came here with honestly $300 in my pocket after I spent the first semester fees and renting a house."

Yamini shares a touching moment with her family:

"I still remember coming down from the conversation with Brian, my kids and my parents were downstairs, and I was crying. And my son looks at me and he says, 'Mom, did you get fired?'"

She recalls her son's concern:

"And he was like, 'What happened? Did you get fired?' And I was like, 'No, I got... Brian wants me to run the company.' And I was literally in tears, super emotional."

Yamini reflects on how becoming CEO was beyond anything she had imagined for herself:

"Never in my life did I think that I was going to be in a public company in a C-suite role, first of all, and certainly not in a public company running it. And that was not part of my vision for myself."

She articulates her original aspirations:

"I wanted to come to this country. I wanted to learn. I wanted to get a good education. I wanted to have a job. I wanted to be economically independent. And I had the fire in my belly to be good at whatever job I did. I wanted to be the best at it."

Yamini emphasizes her focus on growth rather than status:

"It was always about learning and growing and seeing people around me and getting inspired. And it was never about getting to a certain level."

She concludes with a powerful statement about exceeding the American dream:

"People talk about the American dream. Like, this is more than my dream. I did not dream that big. And it was just super emotional to see that Brian and the board had the confidence that I could do something like this."

Yamini expresses her gratitude:

"I consider it my biggest honor and privilege to be leading HubSpot."

Timestamp: [52:04-54:14]

• Yamini's path to becoming CEO began unexpectedly when Brian Halligan texted her on Christmas Eve that she was part of his succession plan, just one year after she joined HubSpot
• When Brian had a serious snowmobile accident in March 2021, Yamini was thrust into the interim CEO role just 15 months after joining the company
• What initially seemed like a temporary arrangement became permanent when Brian returned in July/August 2021 and confirmed she should continue as CEO
• The timing of her appointment coincided with extreme business volatility – first rapid growth during the pandemic, then a sharp market correction
• October 2021 represented the peak of the market, giving Yamini only two months of favorable conditions before the environment changed dramatically
• By April 2022, HubSpot had to "turn the whole ship around" – slowing hiring and recalibrating growth plans due to inflation and rising interest rates
• Yamini's personal journey – from a small town in India without a high school, coming to the US with just $300, to leading a public company – made the CEO appointment deeply emotional
• She describes her achievement as "more than my dream" – beyond even what she had imagined possible within the American dream narrative
• The transition exemplifies how leadership succession can happen unexpectedly, requiring flexibility and readiness
• Yamini's emotional reaction to the news (crying when telling her family) reveals the profound personal impact of her professional achievement

Timestamp: [47:30-54:14]

People:

• Brian Halligan - HubSpot co-founder and CEO for 15 years who appointed Yamini as his successor after a snowmobile accident
• Yamini's son - Asked if she got fired when he saw her crying after learning she would become CEO

Companies:

• HubSpot - The public company where Yamini unexpectedly became CEO

Concepts:

• Succession planning - Process that began informally with a text message on Christmas Eve
• Interim CEO - Yamini's initial role when Brian stepped away for recovery
• Market peak (October 2021) - Referenced as the high point before economic conditions deteriorated
• The American dream - Concept Yamini references as something her achievements exceeded
• Economic pullback (April 2022) - When HubSpot began seeing customer spending slow due to inflation and interest rates
• C-suite - Executive leadership level Yamini never expected to reach in a public company

Timestamp: [47:30-54:14]

Yamini describes how the fundamental challenge of her role changed when transitioning from Chief Customer Officer to CEO, particularly regarding the exponential increase in stakeholders.

"The number of stakeholders that you now have to manage and the almost impossible task in getting everybody's approval at any given time."

She contrasts the relatively straightforward stakeholder prioritization of her previous go-to-market roles:

"When you are in go-to-market roles, very, very clear you're focused on the customers. Customers number one, partner maybe number two, and then your team and employees number three. And you really are focused on these three stakeholders."

Yamini explains her previous framework for decision-making:

"My framework had always been if you can maximize the value for the customer and you can maximize the value for the company and you can line it up for what an individual rep in your organization wanted to do, if you can line it up then you can actually maximize outcomes from all."

She details how this guided her approach:

"Any system I put in place or any product we were trying to sell or any incentive change we're making, it was customer, company, rep. That was what I would base my decisions on."

The CEO position dramatically expanded this framework:

"And now you're in this world where it's certainly customers, it's certainly partners, it's certainly employees, and then you have shareholders. Your ultimate boss is like your investor and shareholder base. And then you have board and managing the board. And then you have founders who are trying to figure out what their life is going to be like after being a CEO for such a long time."

Yamini acknowledges the fundamental challenge this creates:

"What I've recognized is that it's really hard to get it right across all of them. You may be able to get it right for many of them, but if you did something that is really for customers, you might have to delay the impact that it has on your company that then shows up with investors. You can't maximize for all."

She summarizes the complexity:

"It's a very, very difficult set of constraints that are there."

Timestamp: [54:22-56:36]

Yamini reveals a persistent sense of "being behind" throughout her life and career, and how this has actually served as a powerful motivational force.

She begins by noting the perception challenges she initially faced as CEO:

"For me part of it was also, while I started my career as an engineer, I have been in go-to-market for the better part of like two decades. And so the initial question was like, 'How's she going to drive product?'"

This connects to a deeper pattern in her life:

"I've always had this like sense of being behind. You know, I grew up in a small town, which meant that I would look at my cousins and family in bigger cities that had opportunity. I was behind."

Yamini traces this feeling through various life transitions:

"I came to the US, I was behind. It took me a while to kind of get used to a new country with a new system, with new ways of communicating. I was behind. And then I was an engineer behind, trying to become a salesperson. And then I was a go-to-market person behind, trying to help with product."

Rather than seeing this as a disadvantage, she reframes it as fuel for growth:

"If you're behind, what is it that you can do to drive the right outcomes and the results? And maybe that's what gives me the drive... Those are points in time when I feel like I'm behind, which most of my life I feel like I've been behind. It gives me the drive to learn and to grow and to take that as a challenge."

Yamini reveals her mindset for handling this feeling:

"I never take it as a question on me personally. I take it as a question on my experience, and all of those times it was right. It's been this journey of trying to learn and trying to remain very resilient."

Timestamp: [56:36-58:17]

Jubin shares his own feelings of inadequacy, and Yamini responds by describing how she's come to embrace the discomfort of always feeling behind, recognizing it as a driver of her greatest growth.

Jubin admits:

"I always feel behind too. I always feel like I'm not doing enough, I'm not trying hard enough, I'm not producing enough good work. And I always tell myself if I just push a little bit harder, then I will be enough."

He describes chasing "this imaginary dragon of getting over the hill of not enough," while recognizing that this same feeling may be what drives him forward.

Yamini responds with a profound insight about her relationship with this feeling:

"This feeling in my stomach of being behind or getting up in the morning and looking at how much needs to happen - I've embraced it. I've embraced it and made my peace with it because if I look back, those are the times in my life where I've grown the most."

She illustrates with a specific example from early in her career:

"When I was an engineer, I then went to business school and got into my first sales job. I was like, 'I have no idea. I'm an engineer from India and now I have a quota. What am I going to do in this role and how am I going to be successful?'"

Yamini candidly analyzes the challenges she faced in sales:

"I am an introvert. I don't play sports. I don't banter. I was not particularly great at building relationships. Maybe now over the years I've gotten a little bit better, but I have all of the inherent disadvantages of not being successful in sales, and that kept me awake."

Timestamp: [58:17-59:55]

Yamini shares how she discovered her unique strengths by focusing on what she could do well rather than traditional approaches, illustrating how perceived disadvantages can become advantages.

"I was like, 'I'm going to crack this thing.' And what I found is that I was not good in the first five minutes of a sales call, but I was actually very good in the next 25 minutes of the sales call because I used almost an engineer's approach to breaking down the problems and figuring out challenges."

She describes her meticulous preparation process:

"I would read 10Ks, I would read 10Qs, I would listen to company management speak, and then I would ask them a question 10 minutes in and they'd be like, 'That is the biggest challenge that we have.'"

Yamini explains how she leveraged her analytical strengths:

"And then we'll be like, 'Let's go into the challenge. Why have you had that challenge?' And then be present and repeat back to them why that was a challenge."

She came to a breakthrough realization:

"I really suck at that first five minutes, but then I know how to crack the next 25 minutes. Let me just do that. And that made me better as a sales professional in front of customers."

This approach, while requiring significant effort, led to deeper expertise:

"That was hard work, but after like 10 years, I was like, 'I think I've learned so much.' I've learned not only the art of selling, I've learned the actual buying process and the buyer's approach to thinking about investments, and that has helped me in my career."

Yamini connects this back to her broader philosophy:

"I look at periods where I feel like I'm behind and that's when I learned the most. So now I have embraced that discomfort. I've embraced that feeling behind, that thing that you wake up every morning with, and that's helped."

She concludes with a powerful insight:

"You look back at your life and your career and there are things that serve you well and then things that don't serve you well. And things that serve you well, even if they make you feel uncomfortable, it's okay. You embrace it and you kind of go."

Timestamp: [59:55-1:01:50]

Jubin asks about the widely-acknowledged loneliness of the CEO position, and Yamini confirms this reality while explaining the specific constraints that create this isolation.

Jubin poses the question:

"On the stakeholder management thing, do you think that the reason why so many CEOs say that it's really lonely, and then nobody really believes them until they get into the CEO job and then they realize it's really lonely, is because you feel like across all of these stakeholders there's just somebody you're always letting down?"

Yamini immediately confirms:

"Absolutely. And here's the thing - you cannot talk about it."

Jubin interjects with specific limitations:

"You can't talk about it to your team."

Yamini continues:

"No, you can't talk about it to your board."

Jubin adds:

"No, you can't talk about it to another CEO because they don't have enough context on your business."

Yamini affirms:

"I mean it is, it is very, very lonely."

She describes attempts to find community during COVID:

"I've been fortunate where, as we were doing all of this around COVID, we created a CEO group and a network of CEOs because we were all at home, we're all trying to navigate COVID, the pandemic, and every possible twist and turn."

Despite having this network, she acknowledges its limitations:

"Even within that CEO network, they're not going through exactly what you're going through. And I think in almost every other role, you have a set of peers that are going through exactly what you're going through and you can have a conversation with them."

Yamini explains the practical constraints:

"I love my team. I work with them every single day. But if there is a challenge with a member of the board or something else, I'm not going to go and talk to them about it. So you're dealing with that."

She highlights the fundamental accountability that comes with the role:

"At the end of the day, you have to empower your teams and delegate work, and they have to do it. But if something doesn't go well, you are accountable. You're 100% accountable."

Yamini shares how she handles this:

"There are times where I've said to the board that this is on me. Something didn't go well, a bet didn't go well, or a change that we made didn't go well. I know who did it and I'm giving them coaching, I'm giving them guidance, I'm giving them performance reviews, but it is on me. The accountability is on me."

She concludes:

"So it is very lonely. You cannot talk about it."

Timestamp: [1:01:50-1:03:46]

Jubin asks a probing question about Yamini's relationship with HubSpot's founder and former CEO, Brian Halligan, exploring the complex dynamics of succeeding a founder.

Jubin poses the question:

"Can you talk to Brian? He's been the CEO for 15 years. He founded the company. Between him and his co-founder, there's nobody that has more context on the business."

He then adds the emotional complexity:

"But doesn't deep down part of you say, 'I want him to view me as an independent and competent leader'? Isn't there some part of you that's like, 'This is my thing now. I need to put my flavor on it. I can't show him all of my deepest and darkest insecurities because I want him to feel like it's in good hands'?"

Yamini acknowledges this tension:

"I mean, it has been phenomenal to have Brian and Dharmesh [co-founder] during this whole part, and we do have these conversations."

She describes how these interactions can be both validating and complex:

"Sometimes Brian will be like, 'Yeah, that's a problem. I had that problem for 15 years.' So I'm like, 'Okay.' And he'll go, 'I don't have an answer, but you should know that I had the same problem.' And I'm like, 'Okay, thank you. That is validating and that's helpful.'"

Yamini explains how their leadership styles necessarily differ:

"There are other times where he will say that he was a startup-to-scale-up CEO, and I'm trying to do scale-up to grown-up company. And so my decisions might look very different than some of the decisions that he's made, and I would need for him to trust me in making those decisions, and that comes with time."

She concludes by emphasizing the all-encompassing nature of her role:

"It's lonely. It's the most challenging job I have ever done, and I would call it more than a job. It's like it's my life now. It just consumes everything you have in your life, and you got to give it your 200%. There's no other way to do that."

Timestamp: [1:03:46-1:05:28]

• The CEO role dramatically expands stakeholder management from the relatively straightforward "customer-company-rep" framework to include shareholders, board members, and founders
• Unlike other roles, being CEO makes it "almost impossible" to satisfy all stakeholders simultaneously; optimizing for one group often means delaying benefits for others
• Yamini has experienced a persistent feeling of "being behind" throughout her life – from growing up in a small town to navigating cultural transitions to shifting career paths
• Rather than seeing this as a disadvantage, she has embraced this discomfort as a powerful driver of growth and learning
• As an introverted engineer entering sales, Yamini compensated for weaknesses in small talk by developing strengths in deep business analysis and genuine problem-solving
• She used preparation (studying 10Ks, 10Qs, management statements) to identify customer challenges rather than relying on traditional relationship-building approaches
• The CEO position is uniquely lonely because you can't fully discuss challenges with your team (inappropriate), board (they evaluate you), or even other CEOs (lack context)
• A fundamental aspect of CEO loneliness is the asymmetry between delegation (necessary) and accountability (which remains 100% with the CEO)
• Even with supportive founders, successor CEOs face complex dynamics – wanting both guidance and independence, especially when strategic directions must differ
• Yamini describes the CEO role as consuming "everything you have in your life" requiring "200%" commitment – "more than a job... it's my life now"

Timestamp: [54:22-1:05:28]

People:

• Brian Halligan - HubSpot founder and former CEO who Yamini succeeded
• Dharmesh - HubSpot co-founder mentioned briefly (Dharmesh Shah)

Companies:

• HubSpot - The company Yamini leads as CEO

Concepts:

• Stakeholder management - The expanded complexity of balancing interests of multiple groups as CEO
• Customer-company-rep framework - Yamini's previous decision-making approach in go-to-market roles
• 10Ks/10Qs - Financial reports Yamini studied to prepare for sales calls
• Startup-to-scale-up vs. scale-up-to-grown-up - Different CEO roles and styles described by Brian
• The feeling of being behind - Persistent sense Yamini has experienced throughout her life and career
• CEO loneliness - The isolation that comes from having ultimate accountability without peers to fully discuss challenges
• Engineer's approach to sales - Yamini's analytical method that compensated for traditional relationship-building weaknesses

Timestamp: [54:22-1:05:28]

Jubin asks Yamini about the stakeholders she feels she's let down most in her role, leading to a candid discussion about the painful realities of leadership during difficult times.

"Is there a stakeholder that you feel like you let down the most? Like is there a stakeholder that you felt like, 'All right, I took my lumps on this one and I'm going to get better as a result?'"

Yamini's response is both surprising and deeply honest:

"I actually think that it would be employees. I mean, I would say this because we've been fantastic in terms of growth, but then we talked about the challenges of '22, and then we talked about the challenges of what happens when you pull forward demand for many years to come into a couple of years."

She describes the operational challenges this created:

"You grow, you don't have the systems. I think employees were like, 'We can't get work done because there's so much pull forward demand.' And they didn't articulate it that way. They said, 'It's becoming harder to get work done at HubSpot.' And true enough, of course it is, because we haven't built the company for the scale that we are now seeing as a company."

Yamini then addresses the most difficult decision of her tenure:

"And then we had to do a layoff. We've done one layoff. We did it in January 2023."

Jubin interjects, emphasizing the necessity:

"You had to do it."

Timestamp: [1:05:35-1:06:33]

Yamini provides a thoughtful analysis of the layoff decision, its timing, and the personal impact it had on her as a leader.

"Looking back, we pulled the lever to slow down hiring in June 2022, and the earliest indicator that things were going down were April 2022. So from a reaction time standpoint, it was quick, but it was not hard enough. And we'd already hired all these people in 2021."

She describes the emotional weight of the decision:

"I think it was a super hard decision to make. And I think, maybe rightfully so, I lost credibility as a leader having taken that decision."

Yamini acknowledges the shared responsibility while taking personal ownership:

"It was, of course, everybody agreed. The board agreed with me. Brian, Dharmesh agreed with me. But it was my decision."

Jubin directly asks about the impact on her leadership standing:

"You think you lost credibility in the eyes of the employees?"

Yamini responds without hesitation:

"Absolutely. Because you made a commitment to them that this is a great place for them, their families, their careers, and you couldn't meet that commitment. Absolutely."

Jubin notes the broader impact on organizational confidence:

"And some skittishness with everybody else, like, 'Oh geez, like new CEO, here we go.'"

Yamini confirms this perception while describing her approach to rebuilding trust:

"Absolutely lost credibility with employees. And I've explained it to them. I think that I've given the context, and I've showed that, 'Look, everybody else is doing it every year, and we've not, and we really tried to maintain...'"

She shares a personal philosophy that guides her through mistakes:

"I always have this saying where I say, 'Make new mistakes.' You know, if you make a mistake, learn deeply from it and try not to ever do that mistake and make new mistakes. And so I think that's part of the learning."

Yamini concludes with the ongoing challenge:

"Absolutely lost credibility with employees and still trying to make that up. And it's also the context of... it's easy when everybody is winning, is not so easy when you're going through downturns as we have gone through in the last couple of years."

Timestamp: [1:06:33-1:08:13]

Yamini describes the compounding challenges of simultaneously managing economic downturn, technological disruption, and workplace transformation.

"On top of that, let's pivot to AI, let's make a whole roadmap change, and let's figure out how we're going to do work from home and trying to get the productivity up."

She summarizes the cumulative effect:

"It's been fairly tumultuous."

Despite these challenges, Yamini emphasizes their core focus:

"I do think that we've doubled down on customers, we've kept that going, but yes, it's very hard to balance all of that given the circumstances."

Timestamp: [1:08:13-1:08:46]

The conversation shifts to Yamini's personal relationship with rest and relaxation, revealing her intense drive and difficulty disconnecting from work.

Jubin asks:

"Is sitting still difficult for you?"

Yamini responds emphatically:

"Absolutely. Yes."

Jubin probes further:

"Can you like veg out on a couch?"

Yamini's answer is definitive:

"No, I have not been able to veg out on a couch."

When Jubin asks why, Yamini explains:

"The better part of 20 years has been sometimes on the couch but reading, looking at... feeling like you're being productive. Always. I don't think I have sat on the couch without my laptop in 20 years."

Jubin expresses disbelief:

"Come on."

Yamini insists:

"I have not. I think that my kids will now say... my son who is going off to college, and he's like, 'Mom, I have four months with you,' and this is like at 11:00 in the night, and be like, 'Can you just shut down the computer for 5 minutes and talk to me?' And I'm like, 'Yes, yes, I will.' And I do, I try to do it, but it's 11 at night and the whole evening I'm sitting on the couch, he's probably doing something there, and I can't do it."

She connects this to her passion for the industry:

"Again, it's one, so exciting. The industry has always been like this. I tell people, 'Don't join tech if you don't want change. If you want a nine-to-five job in a status quo industry where your skills are improving 1% a year, don't join this.' Because this is a vibrant industry. You're making changes all the time. You're constantly learning."

Yamini reveals how this connects to her deeper motivations:

"And for me, if I'm not learning... I already have this mental anxiety of I'm behind from where I came up, so I'm always like, 'If I'm not learning, I'm behind.'"

Timestamp: [1:08:46-1:10:28]

Jubin pushes Yamini on her relationship with rest, and she reveals the careful balance she's created to sustain her energy and creativity without burning out.

Jubin observes:

"So you feel like if you're not learning, you're just completely wasting your time?"

Yamini confirms:

"Yeah, yeah."

Jubin then asks about the concept of slowing down:

"But what happens if you want to... how do you slow down? Is there such thing?"

After Yamini acknowledges that slowing down is possible, Jubin refines his question:

"Do you feel the need to slow down, meaning like, do you need a break from something that gives you so much energy and excitement?"

Yamini reveals that she has developed a system for balance:

"I do. So I'll say that my Saturdays are precious to me because it is really a time I... my husband and I go for a long walk. I do yoga. I do meditation. So those days are good."

She also describes her approach to vacations:

"And then we take vacations, and we go on vacations. The first three, four days I'm like, 'Okay, what's going on in the world?' And then the next seven days, I actually get into it. Whether it is going somewhere or going on a retreat, whatever it is, I sink into that moment. And then the last three days I'm like, 'Let me get back.'"

Jubin asks a pointed question about her ability to disconnect:

"When on a Saturday, do you not feel that urge to check your email? Is that gone?"

Yamini explains that she's developed this discipline out of necessity:

"It is gone because I will tell you what the alternate... When I did not do that, when I didn't take breaks, whether it was a vacation or my Saturday, I got burnt out pretty quickly. I would get into this place where I was burning out by June, July in a year. I'd be like, 'I'm so exhausted, I can't function.'"

She connects rest to creative capacity:

"And I also think that creativity actually slows down if you don't get a break."

Yamini describes her structured approach to daily rejuvenation:

"For me, every evening I take like an hour, either I'm doing yoga or doing some kind of workout or walking or listening to music. That is a break. My Saturdays are break. So I have like inbuilt breaks."

She concludes by noting that even her relaxation tends to be mentally engaging:

"And then I'll take longer vacations. But even in the vacations, my idea of a good time is reading a great book. That is my idea of a good time. So I'll put down my laptop, but I'm reading some..."

Timestamp: [1:10:28-1:12:26]

• Yamini identifies employees as the stakeholders she feels she let down most, particularly through the January 2023 layoffs
• Though she acted relatively quickly to slow hiring in June 2022 (just two months after seeing warning signs), the action "was not hard enough" given previous hiring
• She acknowledges losing credibility with employees after breaking the implicit promise that HubSpot would be "a great place for them, their families, their careers"
• Yamini's leadership philosophy includes "make new mistakes" - learning deeply from errors but not repeating them
• The layoffs occurred during a period of "tumultuous" change that included economic downturn, AI pivot, roadmap changes, and remote work productivity challenges
• Yamini has not "sat on the couch without my laptop in 20 years" - illustrating her difficulty disconnecting from work
• Her difficulty resting connects to a deeper anxiety about "being behind" - if she's not constantly learning, she feels she's falling further behind
• After experiencing burnout ("by June, July... I'm so exhausted I can't function"), she developed a structured approach to breaks
• Her system includes daily breaks (yoga, workout, walking, music), protected Saturdays (no email checking), and longer vacations
• Even during relaxation, Yamini tends toward mentally engaging activities like reading, rather than fully "vegging out"
• She recognizes that creativity suffers without proper breaks, creating a practical incentive for maintaining balance

Timestamp: [1:05:35-1:12:26]

People:

• Yamini's son - Mentioned as asking her to shut down her computer to talk for 5 minutes at 11 PM before leaving for college
• Yamini's husband - Mentioned as her walking companion on Saturdays
• Brian - Referenced as agreeing with the layoff decision (Brian Halligan, former CEO)
• Dharmesh - Referenced as agreeing with the layoff decision (Dharmesh Shah, co-founder)

Companies:

• HubSpot - The company where Yamini is CEO and implemented layoffs in January 2023

Concepts:

• Pull forward demand - The pandemic phenomenon where future growth was compressed into a shorter timeframe
• Losing credibility - The leadership impact of making difficult decisions that affect employees' lives and careers
• "Make new mistakes" - Yamini's philosophy about learning from errors without repeating them
• Burn out - The exhaustion that Yamini experienced when not taking proper breaks
• The three phases of vacation - Yamini's description of the adjustment period (3-4 days), immersion (7 days), and anticipatory return (last 3 days)
• "Sitting still" - The challenge of truly disconnecting from work and productivity

Timestamp: [1:05:35-1:12:26]

The conversation shifts to Yamini's unusual reading habits, revealing another dimension of her multitasking tendencies and intellectual curiosity.

Yamini reveals a surprising approach to reading:

"Mostly I read like four books at a time because I don't have the patience to finish a book."

Jubin expresses disbelief:

"Are you serious? I can't ever finish a book."

He asks for clarification about her method:

"So when you travel, you bring four books with you? And they're all physical?"

She confirms her preference for physical books:

"You can't... of course you can't use a Kindle. I mean, Kindle... I don't like it either. I read a lot of magazines and articles online, but I think for me a book is like a physical book."

Jubin seems amazed by her approach:

"You actually packed four books with you?"

Yamini confirms:

"Oh yeah."

Jubin tries to understand her process:

"And then you read them concurrently? Like, you'll read a chapter, you be like, 'All right, I'm done with this for now.' You go to another book, you read a different..."

Yamini acknowledges:

"I parallel read."

Timestamp: [1:12:31-1:13:08]

Yamini shares insights about her eclectic reading choices, from dense intellectual works to popular non-fiction, demonstrating the breadth of her curiosity.

Jubin offers a theory about business books:

"Don't you think that some of these business books, you read two chapters and then you're kind of like, 'I got it,' and then the next eight chapters are like proving two points from the first two chapters?"

Yamini acknowledges this point:

"That's fair."

When asked about her book selection, she reveals:

"Some of them are business books, some of them are like super dense. Like I've been trying to read Gödel, Escher, Bach. Have you read this?"

Jubin responds humorously:

"No, but even just the name makes me think I'm probably not qualified."

Yamini admits her own challenge with the book:

"I myself, I'm not qualified. So this book I can maybe read 10 pages at a time. It is math, its architecture and music, and the commonality across all of this. And it's beautifully written, but very intense, and I can only read 10 pages at a time."

She contrasts this with another current read:

"And then I'm reading Sapiens, and I'm on like probably chapter five now of that. And I can only read one chapter at a time."

Timestamp: [1:13:08-1:14:08]

Jubin and Yamini discuss the psychology of reading and how giving oneself permission to abandon books can actually encourage more reading.

Jubin shares his own evolving approach:

"I used to feel like I had to finish books just out of like a commitment. Like, I started a book, I got to finish it."

He mentions a perspective that changed his thinking:

"It was Naval. I just heard him on a podcast talking about how he's like, 'I never finish books. I never feel pressure to finish books. I go back to books, I highlight books.' He's like, 'But if I don't feel like I want to finish a book, I move on to the next one.'"

Jubin explains the rationale:

"Because he's like, 'That's when you stop reading, is when you feel like you have to finish a book. It's sitting on your bedside table.' And you're like, 'Don't give yourself permission to go to the next book because you're like, No, I got to finish this book.' Then you just stop reading because you'd rather just not read the shitty book you're reading."

Yamini enthusiastically agrees:

"Totally, and this is why I've given the permission."

Timestamp: [1:14:08-1:14:51]

Yamini shares a touching childhood memory about her relationship with books, revealing how reading shaped her worldview and nurtured her curiosity from an early age.

"When I was growing up, I was in this small town, and I still remember the librarian in my town saying... and I would not even go to the library. I'd ask my mom to bring these... I'd write down titles, and my mom would bring it, and I would be reading it."

She explains how this habit reflected her personality:

"This was my introverted self back then."

Yamini recounts a memorable interaction:

"The librarian once said, 'Your daughter has read every book in this library, please don't come here.' My mom said, 'She said that you've read every book in the library.'"

She explains what books meant to her:

"This was my window into the world. This is what cost me the curiosity about the world."

Yamini concludes by describing her ideal day of relaxation:

"For me, the best idea of a Saturday is a long walk, a little bit of yoga, and a book. And one chapter of the book, not more."

Timestamp: [1:14:51-1:15:39]

As the interview winds down, Jubin asks about HubSpot's current hiring priorities, revealing the company's ongoing focus areas.

Jubin expresses appreciation for the conversation:

"I really appreciate you doing this. Thank you. I really do. You're wonderful."

Yamini responds warmly:

"Thank you."

Jubin then asks about HubSpot's hiring status:

"Are you hiring?"

Yamini enthusiastically confirms:

"Yes, absolutely."

When asked about specific roles, she identifies two key areas:

"Any R&D? Sales? We want to build product, we want to sell product. Yes, absolutely. We are continuing to hire them."

Timestamp: [1:15:39-1:15:54]

In the final question, Jubin asks Yamini to define "grit," leading to a powerful reflection on intentional choices and resilience that encapsulates her life philosophy.

Jubin asks:

"When you hear the word grit, what do you think of?"

Yamini responds with a thoughtful definition that connects to her life journey:

"I think of the intentional choices I have made and the resilience to follow through with those intentional choices."

She illustrates with examples from her own path:

"Coming to America was an intentional choice. Being an engineer back in the 80s-90s in India was an intentional choice. Going to sales and trying to make it in sales was an intentional choice."

Yamini articulates her philosophy:

"For me, it is making intentional choices that might not always be conventional wisdom and having the resilience to see it through."

She acknowledges the universal pattern of challenges:

"Every everything that we do in life, there will be good days and bad days. There will be great highs and low lows. And everything has to start with having the resilience to see what you want to accomplish in that."

Yamini concludes:

"So that's what grit has been for me."

Timestamp: [1:15:54-1:16:45]

Jubin closes the interview with gratitude and information about the podcast.

"I can't wait to see what choices you make, what choices you make next."

Yamini responds graciously:

"Thank you, Jubin. Thank you. Thank you so much. Such a pleasure to connect with you."

Jubin provides closing information about the podcast:

"That's it for now. If you like the episode, please leave us a review or go back into the archives where we've done more than 200 episodes with some fantastic folks. This podcast is a Kleiner Perkins production, and I'm Jubin. Thanks for listening."

Timestamp: [1:16:45-1:17:08]

• Yamini reads four books simultaneously, demonstrating her multitasking approach to learning and intellectual curiosity
• She prefers physical books over digital formats, despite consuming online articles and magazines
• Her reading spans from dense, intellectual works (Gödel, Escher, Bach) to popular non-fiction (Sapiens), showing the breadth of her interests
• Yamini has given herself "permission" to read books in a non-linear way, following Naval Ravikant's philosophy that this approach encourages more reading
• Books were her "window to the world" from childhood, to the point where she had "read every book in the library" in her small town
• Her introverted nature as a child manifested in having her mother retrieve library books rather than going herself
• Yamini's ideal relaxation includes a long walk, yoga, and reading just one chapter of a book
• HubSpot is actively hiring in two key areas: R&D (product building) and sales (product selling)
• Yamini defines "grit" as "the intentional choices I have made and the resilience to follow through"
• She sees her major life decisions (coming to America, becoming an engineer, shifting to sales) as intentional choices that went against conventional wisdom
• Yamini's philosophy acknowledges that all worthwhile pursuits include "good days and bad days" and require resilience to achieve meaningful goals

Timestamp: [1:12:31-1:17:08]

Books:

• Gödel, Escher, Bach - A dense intellectual work about math, architecture and music that Yamini reads 10 pages at a time
• Sapiens - Book by Yuval Noah Harari that Yamini is reading one chapter at a time

People:

• Naval - Referenced by Jubin as someone who advocates not feeling obligated to finish books (Naval Ravikant)
• Yamini's mother - Mentioned as retrieving library books for Yamini as a child
• Librarian - Person who told Yamini's mother that her daughter had "read every book in this library"

Companies:

• HubSpot - Yamini's company, currently hiring in R&D and sales
• Kleiner Perkins - Venture capital firm producing the podcast, where Jubin is a partner

Concepts:

• Parallel reading - Yamini's approach of reading multiple books simultaneously
• Grit - Defined by Yamini as making intentional choices and having resilience to follow through
• "Window into the world" - How Yamini describes what books represented to her growing up
• Intentional choices - Major life decisions that may go against conventional wisdom
• Physical vs. digital books - Yamini's preference for traditional book format

Timestamp: [1:12:31-1:17:08]