South Park Commons is a community for people navigating what they want to do next in their careers. Their ethos is about helping members "navigate the idea maze together" and "build your life's work." They have physical spaces in San Francisco and Bangalore, welcoming those considering starting their own companies.

The host introduces Lindsay Kaplan, co-founder of Chief, describing it as "one of the most talent-dense networks of women" and noting that members have consistently praised their experience with the organization.

Lindsay is not only a successful founder but also works as an early-stage investor, collaborating with founders at a similar stage as many SPC members.

Timestamp: [0:00-1:44]

Lindsay Kaplan's career path to entrepreneurship wasn't conventional. With no formal tech background, she began in traditional media, working first in book publishing and magazines before moving to an ad agency. Around 2010, she recognized the emerging importance of social media platforms like Facebook and Tumblr, which led her to transition into putting brands on social media.

Eager to be directly involved in the tech world, Lindsay joined several early-stage startups that ultimately didn't find product-market fit or suffered from leadership issues. These experiences left her questioning her abilities and wondering if she was simply "terrible at this."

"I got really burned out and thought like maybe I'm just terrible at this, maybe I have bad luck, maybe I'm a horrible marketer. I felt like I knew what to do but I couldn't actually get these startups off the ground as the marketer."

Her career took a decisive turn when she received an unusual LinkedIn message with the subject line "mattresses question mark" from the future founder of Casper. Despite the strange approach, Lindsay decided to take one more chance on startups, thinking, "If this one fails, I'm going to either move to the woods and write a novel or go to business school."

Timestamp: [1:45-4:38]

Lindsay joined the then-unnamed mattress startup as the first employee pre-launch. This company eventually became Casper, which grew into a massive direct-to-consumer sleep company. During her four and a half years there, she helped grow the business from pre-launch through Series B funding and beyond.

The experience at Casper transformed Lindsay's self-perception and professional confidence. What began as potentially her last attempt at startup success before a career change became the catalyst for her own entrepreneurial journey.

"I decided these guys are smart but like I can do this right? Like I am pretty qualified. So like what a turnaround story from me thinking 'I'm going to completely leave New York because I'm terrible' to feeling such ridiculous confidence that I thought with my co-founder I would go and do it myself."

This newfound confidence led Lindsay to find her co-founder, raise seed funding in 2018, and launch Chief in 2019. The company eventually raised a total of $140 million, making it "one of the fastest female-led companies to get a billion-dollar valuation" at the time.

Timestamp: [4:38-5:44]

When finding her co-founder Carolyn, Lindsay prioritized complementary differences rather than similarity—a factor she believes many co-founders overlook. While many founding teams come from identical educational or professional backgrounds, Lindsay and Carolyn brought diverse perspectives and skill sets to their partnership.

Carolyn had experience in early-stage startups but also attended Harvard Business School, with expertise in finance and operations—she "loved spreadsheets." Lindsay's background was in communications, brand development, design, and storytelling. This diversity in their approaches became a strength of their partnership.

"What we found was those differences were really complementary, and the test was could we get to the same answer of the question and like get there in a completely different way? Her way ended up being logical and the math... and mine would be the gut-driven creative psychological way in."

Despite their different approaches, they typically arrived at the same conclusions, which Lindsay found powerfully affirming. When you have "somebody with a completely different skill set agreeing with you and getting there a different direction," it validates the decision even more.

Equally important, they shared core values stemming from similar upbringings in small towns in upstate New York and middle-class backgrounds. Both had "forged their way into the startup world" and shared similar attitudes and perspectives.

"You kind of want somebody that you will both roll your eyes at the same thing. That's how you know your values are aligned."

Timestamp: [5:45-8:36]

Unlike many startup stories that involve multiple pivots or completely abandoned concepts, Chief's initial idea remained remarkably similar to what exists today. Lindsay acknowledges this is atypical and not necessarily something to emulate, but it worked for them.

Chief was modeled after an existing business that was already working well. Lindsay emphasizes that successful ideation often doesn't require invention from scratch:

"When people are thinking about idea generation, people are looking for an invention, and so often you don't need to invent anything. There are no new ideas. Every idea has been done. To me, it's more about finding something that can be repurposed for a new audience."

She draws a parallel to her experience at Casper, noting that selling mattresses in a box wasn't new—there was literally a company called "Bed in a Box." What Casper did differently was wrap the concept in a completely different brand targeted at millennials.

This philosophy suggests that innovation can come from thoughtful adaptation rather than pure invention, focusing on how existing successful models can be repositioned for different audiences or with fresh branding.

Timestamp: [8:37-9:57]

Despite her non-traditional path to entrepreneurship, Lindsay recognized in retrospect that certain aspects of her personality and childhood might have predisposed her to become a founder. She reflects on the seemingly disconnected elements of her background that, in hindsight, pointed toward her entrepreneurial future.

"I have no idea how I became a Founder because if you looked at my resume it just does not... I have no Tech background at all."

She notes that spending her "formative years very nerdly" on a 386 computer playing Oregon Trail might have been an early indicator. Being "a loner that read a lot of books" also contributed to her development as an independent thinker.

Perhaps most tellingly, Lindsay identifies a core personality trait common to many founders:

"I absolutely hate when people tell me what to do. I don't know if anybody here feels that way—Founders welcome."

This comment, which resonated with many in the audience, highlights how certain personality traits—independence, resistance to authority, intellectual curiosity—often manifest early and may predispose individuals to entrepreneurship, even when their formal career path doesn't initially point in that direction.

Timestamp: [2:06-2:44]

• Non-traditional career paths can lead to successful entrepreneurship - technical backgrounds aren't essential
• Early career setbacks and failures can eventually build confidence and resilience for founding a company
• Complementary skills and perspectives between co-founders can be more valuable than similar backgrounds
• Shared core values between co-founders are essential, even when their approaches differ significantly
• Innovation often comes from repurposing existing successful models for new audiences rather than inventing something entirely new
• Personality traits like independence, curiosity, and resistance to authority often indicate entrepreneurial potential
• The confidence to start a company can emerge from seeing others succeed and realizing "I can do this too"
• Career transformations can be dramatic - from questioning one's abilities to leading a billion-dollar company
• Community spaces like South Park Commons play an important role in helping potential founders navigate their next steps

Timestamp: [0:00-9:57]

Companies/Products:

• Chief - Lindsay's company, a network for senior women executives
• Casper - Direct-to-consumer mattress company where Lindsay worked as first employee
• South Park Commons - Community for people navigating what to do next in their careers
• Facebook - Mentioned as an emerging social platform around 2010
• Tumblr - Mentioned as an emerging social platform around 2010
• Foursquare - Mentioned as an emerging social platform around 2010
• Bed in a Box - Company mentioned as selling mattresses in boxes before Casper

Educational Institutions:

• Harvard Business School - Where Lindsay's co-founder Carolyn studied

Media/Entertainment:

• Oregon Trail - Computer game Lindsay played in her youth on her 386 computer

Locations:

• San Francisco - Location of South Park Commons physical space
• Bangalore - Location of South Park Commons physical space
• New York - Where Lindsay was based during her career struggles
• Upstate New York - Where both Lindsay and her co-founder grew up in small towns

Timestamp: [0:00-9:57]

Building on her philosophy that innovation often comes from repurposing existing models, Lindsay explains how Chief took the concept of an executive network and rebranded it for a new audience. Just as Casper had rebranded the mattress-in-a-box concept for millennials, Chief reimagined what an executive network could be.

The idea for an executive women's network wasn't new—numerous women's executive networks already existed. However, Lindsay didn't find any of them appealing to her personally.

"I just didn't want to join any of them. Like they sounded horrible to me, and I felt like if I didn't want that, there was nothing that was appealing to somebody who was like a different breed of executive woman."

The innovation wasn't in creating an executive network for women from scratch but in executing and branding it differently, finding the right market segment that was previously underserved. Chief targeted what Lindsay calls "a different breed of executive woman"—leaders who weren't connecting with traditional networking options.

The specific idea came from Lindsay's co-founder Carolyn, who was inspired by YPO (Young Presidents' Organization), an existing executive network that was approximately 90% men due to its qualification requirements. Despite its demographic imbalance, YPO demonstrated excellent member retention and engagement—qualities they wanted to replicate for women executives.

Timestamp: [9:57-11:55]

Raising Chief's seed round in 2018 was far from the smooth, immediate success that some entrepreneurial stories might suggest. Lindsay describes it as "the most demoralizing month" of her life, filled with constant rejection.

"It was horrible. So many nos. All nos."

Lindsay offers a keen observation about venture capital dynamics: despite VCs' emphasis on data rooms, product demos, and résumés, they ultimately "operate emotionally" like all humans. This creates predictable but challenging patterns in fundraising:

"What do people want? People want what they can't have. People want what other people want. The nos feel like they just stack on, and the second you have a yes and you share that yes with somebody else, all of a sudden 'Oh really, that other VC is interested?'"

While this pattern might be predictable in retrospect, Lindsay emphasizes that "when you're in it, those NOs sting so hard." After numerous rejections, they finally secured one "yes" that gave them the confidence to pursue more opportunities, creating momentum in their fundraising efforts.

Another challenge was processing the feedback that accompanied each rejection. When feedback consistently points to the same issues, founders can identify clear problems to address. However, Lindsay and her co-founder received widely varying feedback from different VCs, making it difficult to determine whether they should pivot or modify their concept.

Ultimately, they decided to "stick to our guns" with their original idea precisely because the negative feedback was so inconsistent—a decision that led to their eventual success.

Timestamp: [12:02-14:05]

While many founders focus on perfecting their pitch, Lindsay's breakthrough in fundraising came through a chance personal connection. During a venture capital meeting, she unexpectedly encountered a mutual acquaintance working at the firm.

"I walked into a VC office and one of the guys was like 'Wait, are you Dan's friend?' and I was like 'I could be... who's Dan?'"

This serendipitous connection created an immediate rapport that changed the dynamic of the meeting. The VC was more receptive and, in Lindsay's words, "kind of rooting for me" because of this loose connection—highlighting how venture capital, despite its data-driven appearance, remains fundamentally human and relationship-based.

Lindsay extracts a crucial lesson from this experience: successful fundraising requires more than just a great product or pitch.

"When you go out to raise money, you have to meet people. You have to put yourself into awkward situations. You have to shake hands. You have to go to the lunches, the dinners, the speaking engagements."

She emphasizes that being a founder demands excellence in two distinct areas:

"You have to make a great product, and you also have to be a storyteller—because you're going to have to storytell to investors, you're going to have to storytell to employees. It is about being a people person if you want to be a founder."

This insight underscores the importance of network-building and maintaining loose connections, which Lindsay notes is especially advantageous in New York's relationship-oriented business ecosystem.

Timestamp: [14:06-16:33]

After successfully raising their seed round, Lindsay faced the question that confronts many first-time founders: what to do with the money? While many might jump straight to product development or marketing, Lindsay's first priority was more practical and personal.

"Immediately give myself a salary. True story. I had a kid... Immediately give myself a salary."

She emphasizes this point strongly, recognizing a tendency among some founders to undervalue their own financial needs:

"I'm going to say that again: give yourself a salary and pay yourself because you should. You need to be able to put food on your table and not be freaking out so you can focus on your business."

With this fundamental need addressed, Lindsay and her co-founder focused on two parallel tracks: pre-selling their concept to potential customers while simultaneously building what would become their offering. This work through the fall of 2018 culminated in Chief's official launch in February 2019.

The launch was impressive by any standard, especially for a membership-based business. They secured a physical space in Tribeca, New York, and had already signed 200 paying members who each invested between $5,000 and $7,000 for membership. This demonstrated remarkable early traction and revenue generation before their doors even opened.

When they later sought Series A funding, some investors assumed these early customers were simply friends and family connections. Lindsay quickly corrected this misconception:

"All the meetings they were like, 'Okay, you tapped your friends. Now what?' And I was like, 'Oh sir, these are not my friends. I do not know these ladies. I have no friends.'"

Timestamp: [16:34-18:16]

Rather than relying on personal networks, Lindsay and her co-founder took a bold approach to acquiring their first members: cold emailing executives. This strategy paid off in a significant way when they landed their first major customer.

"The first person who paid—so Chief is an executive network for women—we cold emailed executives, and the first person who paid was the chief customer officer of Walmart."

This initial high-profile customer became a powerful selling point that created a snowball effect in their recruitment efforts. Lindsay explains their subsequent approach:

"Then we started telling other people, 'Join us! We have members like the chief customer officer of Walmart.' And so that started to snowball."

This illustrates the powerful role that social proof plays in customer acquisition, particularly for exclusive membership organizations. Having a recognized executive from a massive company like Walmart provided instant credibility that helped attract additional members.

By the time they launched in February 2019, this approach had secured them 200 paying members, each paying between $5,000-$7,000. As Lindsay put it simply: "we were making bank." This early traction demonstrated not only the viability of their concept but also their ability to execute effectively on member acquisition.

Timestamp: [18:17-18:52]

Despite Chief's impressive initial traction with 200 paying members at launch, Lindsay is candid about the operational realities they faced: success didn't mean everything was smooth sailing. When asked if things were just "working and working out," her response is emphatic:

"No! Immediately there's problems. Immediately! Because it's a startup."

The early days presented numerous operational challenges. They lacked a technology platform to support their growing community and were sending event invitations manually. As Lindsay describes it, "everything's a mess."

Yet amid these growing pains, they experienced rapid organic growth. Their events quickly developed waitlists as membership expanded:

"We start all of a sudden we have 300 people, 500 people, 800 people."

Rather than waiting to solve all these operational challenges before seeking additional funding, Lindsay and her co-founder made a strategic decision to capitalize on their momentum and raise a Series A round immediately after launch. Her reasoning reveals a sophisticated understanding of investor psychology:

"When you don't need money, you should go out and raise money. Because VCs are emotional, and people want what they can't have, and people want to bet on a winner."

This approach paid off tremendously. They raised their Series A in spring 2019, just months after their official launch. They went into the fundraising process hoping to raise $20 million but ultimately secured double that amount—$40 million—a testament to both the strength of their vision and the effectiveness of their fundraising strategy.

Timestamp: [18:53-19:53]

• Innovation often comes from reimagining existing business models for new audiences rather than creating something completely novel
• Successful fundraising requires persistence through numerous rejections before finding investors who align with your vision
• Inconsistent feedback from VCs can actually be a sign to maintain your original vision rather than pivot
• Personal connections and relationships play a crucial role in fundraising success, highlighting the emotional aspects of venture capital
• Founders should prioritize paying themselves a reasonable salary to maintain focus and reduce personal financial stress
• Cold outreach to potential high-profile customers can be effective when targeted carefully
• Landing prestigious early customers creates powerful social proof for recruiting subsequent members
• Even successful startups face immediate operational challenges and "messes" behind the scenes
• Strategic timing for fundraising can be critical—raising money "when you don't need it" can lead to better terms and larger rounds
• VCs respond to momentum and social proof—they "want to bet on a winner" and "want what they can't have"
• Storytelling abilities are as important for founders as product development skills

Timestamp: [9:57-19:53]

Organizations/Networks:

• Chief - Lindsay's executive network for women
• YPO (Young Presidents' Organization) - Executive network that was 90% men, used as inspiration for Chief
• Walmart - Company where Chief's first paying member (Chief Customer Officer) worked

Places:

• Tribeca - Location of Chief's first physical space in New York City
• New York - Referenced as a city where networking and connections are particularly valuable

Funding Rounds:

• Seed Round - Raised in 2018, described as a challenging experience with many rejections
• Series A - Raised in spring 2019, sought $20M but raised $40M

Concepts/Terms:

• D2C/DTC (Direct to Consumer) - Business model mentioned in context of Casper and the "zeitgeist" of the time
• Pre-selling - Strategy used by Chief to secure customers before official launch
• Social proof - Concept utilized when leveraging high-profile early members to attract others

Timestamp: [9:57-19:53]

The stark contrast between Chief's seed and Series A fundraising experiences illustrates the dramatic shifts that can occur in the startup journey. After enduring "99 Nos" during their seed round, Lindsay and her co-founder returned to San Francisco for their Series A and encountered a completely different reception.

"It was bizarre. Like we had all of these Nos and all of a sudden we had the complete opposite problem where we were getting wined and dined."

This dramatic reversal led to a bidding war among investors, a remarkable turnaround from the rejection they had faced previously. The experience was so surreal that it produced unexpected physical effects—Lindsay reveals a personal side note with humor:

"I was so nauseous. I threw up outside of Andreessen Horowitz. My co-founder looked at me and she was like 'Are you pregnant?' And I was... I was pregnant."

She quickly reassures the audience about her son, now four years old: "He's fine. He plays chess, he's fine." This humorous aside reveals the very human and sometimes messy reality behind the glossy exterior of successful fundraising rounds.

The shift from widespread rejection to enthusiastic interest underscores how quickly investor sentiment can change once a startup demonstrates traction and momentum. It also highlights the emotional rollercoaster that founders experience, with extremes of both rejection and validation occurring in quick succession.

Timestamp: [20:00-20:51]

The timing of Chief's growth presented a unique challenge when COVID-19 hit. Lindsay describes how Chief "never had a normal year of business" after their explosive launch in 2019. In a stroke of unfortunate timing, the company had signed "a bunch of really expensive real estate deals" that closed in January 2020—just before the pandemic shut everything down.

"We were at the top of the conversation with all of our investors that like we were just a write-off. Like this thing is going to be dead in the water."

The pandemic created an existential crisis for Chief, which had built its business model around in-person connection and physical spaces. Lindsay compares the pandemic's impact to a tsunami:

"It either took you out or you could ride it, and we somehow rode it."

The company made a rapid pivot to fully digital operations, which unexpectedly enabled them to expand nationally much faster than their original plan. What seemed like a potential business-ending disaster became a catalyst for accelerated growth.

This pivot wasn't without consequences, however. When in-person gatherings resumed, Chief faced a new challenge: members across the country who had joined during the digital-only period now wanted local clubhouses and in-person experiences. This created operational scaling problems that might have been avoided with a slower, more traditional geographic expansion.

Lindsay reflects that this rapid growth, while positive in many ways, masked underlying operational issues:

"The growth could hide some of the problems, and that's the scary thing about growth. You want it so badly, and then when you actually achieve growth, it does mask some of the issues underneath that will eventually come back and get you."

This insight reveals the double-edged nature of rapid scaling—problems that might have been addressed early can be obscured by positive growth metrics, only to resurface later as more significant challenges.

Timestamp: [20:52-22:51]

When asked about the lowest point in Chief's journey, Lindsay doesn't hesitate—it was the early weeks of the pandemic in 2020 when they were forced to completely reimagine their business model. This period represented a genuine existential threat, especially as they watched similar community-based businesses collapse around them.

"I don't know if people remember The Wing—The Wing went under, and WeWork went under. Again, we were in-person."

These high-profile failures of well-funded, space-based community businesses made Chief's prospects seem equally dire. Yet, they managed to survive and ultimately thrive. Lindsay attributes this survival to several factors that aligned in their favor:

"I think we were very fortunate—this is like right time, right place, right market, right customer."

Chief's membership base—executive women—turned out to have unique needs during the pandemic that the organization could satisfy even without physical spaces. The isolation of lockdowns actually heightened the value of Chief's offerings:

"Our customers wanted connection, they needed Chief. They didn't care about the in-person experience right now—they just were lonely and freaking out and had all of this work pressure."

As the initial panic of 2020 subsided, another fortunate market condition emerged that further benefited Chief—companies became increasingly focused on executive retention and development:

"Once the panic of 2020 subsided, there was robust employer spending, and employers wanted their executives, and they wanted retention. There were bonuses."

This combination of member need and corporate willingness to fund professional development created conditions that allowed Chief not just to weather the storm but to accelerate growth during a period that devastated similar businesses.

Timestamp: [22:52-24:11]

When asked how Chief was able to pivot so effectively during the pandemic crisis, Lindsay emphasizes the importance of building a team capable of rapid adaptation. She highlights the advantage that startups have over larger organizations—the ability to change course quickly when necessary.

"I think surrounding yourself with people who can be nimble and love a challenge and want to move quickly."

Lindsay and her team embraced the need for swift action, though she notes with humor how they tried to frame their approach: "We were joking like 'We're not reactive, we're responsive!'" This distinction, while partly in jest, reflects a deliberate mindset of proactive adaptation rather than panicked reaction.

She contrasts this startup agility with the frustrating inertia often experienced at larger companies:

"If you've ever worked at a big company, you could see an iceberg and you're like 'We're in this big boat... why are we doing this?' I've worked at those big companies. It's the most painful thing, and everybody sees it. It's just so hard to move a giant ship."

This observation resonates with the audience of aspiring founders at South Park Commons, many of whom have likely experienced similar frustrations in corporate environments. Lindsay suggests that this very frustration is what drives many people toward entrepreneurship:

"The executives know, typically, at these giant companies when something bad is coming. They've just already placed the bets, they've already raised against this money—they can't move the ship in time."

In contrast, she describes the startup advantage as "the luxury of being little" and finding team members "who want to get in a kayak and just be as nimble as possible and navigate that chop." This nautical metaphor aptly captures the difference between corporate inertia and startup maneuverability, particularly during crisis situations.

Timestamp: [24:12-25:53]

When asked about her motivation and the impact Chief is having, Lindsay draws an interesting distinction between her organizational mission and her personal drive. These dual motivations reveal the complex interplay between social purpose and individual ambition that often fuels successful founders.

Chief's mission focuses on addressing systemic gender disparities in leadership:

"My motivation for Chief was very much building a space where women could aspire to. Most executive teams are men. Women typically feel othered, and in order for women to achieve parity, they need to be in communities. They need to feel comfortable and confident and have those spaces where they feel like it is their room."

This articulation of Chief's purpose highlights Lindsay's understanding of the structural challenges women face in reaching and succeeding in executive positions. She identifies the importance of creating environments where women executives don't feel like the exception or the "other."

However, when describing her personal motivation, Lindsay reveals a different, more internally-driven source of energy:

"My personal motivation is often just proving people wrong, and I am just fueled by competitive anger because I don't like when people tell me what to do, and I like to be in rooms that I'm not supposed to be in."

This candid admission about being "fueled by competitive anger" resonates with many in the audience. Lindsay suggests this trait is likely common among the aspiring founders at South Park Commons:

"I assume the people that are in this room—there's a reason you are either not in corporate or left corporate or want to leave corporate. It's because you want to be in rooms that you were not invited into. You don't want to be told what to do, and you enjoy proving people wrong and thinking about things differently."

She concludes with a personal philosophy that encapsulates her entrepreneurial spirit: "Life is really boring if you don't try to see what's behind the door." This statement captures the curiosity and boundary-pushing drive that propels many successful founders beyond conventional career paths.

Timestamp: [25:54-27:55]

As an investor working with early-stage founders, Lindsay offers two distinct pieces of advice—one she finds herself giving more frequently to women founders, and another that applies broadly to all entrepreneurs.

For women founders specifically, Lindsay encourages greater boldness in fundraising:

"The advice I more often give to women than men—and this is not exclusive—is to raise more money and just go for it and just do it and be bolder."

While acknowledging she doesn't want to overgeneralize, Lindsay observes a pattern of greater conservatism among women founders. She notes this caution might actually be beneficial later in a company's development, as women-led businesses often "perform better [and] have lower rates of burn." However, at the earliest stages, she advocates for a more aggressive approach:

"Early on, just if you're going to do it, just do it and raise as much money. Start a process, go do it, and just be bold and confident."

Her second piece of advice, which she gives to founders regardless of gender, addresses a common pitfall—emotional attachment to ideas that don't make viable businesses:

"Sometimes people are married to an idea they love that isn't always a good business, and just because it's a good idea and you like it doesn't mean it's a great business."

She particularly highlights the importance of recognizing when an idea might be valid but not suited for venture capital:

"Sometimes it's not a VC-sized business, and that is really hard to hear, especially for folks that view venture as so prominent and view that as kind of the goal."

Lindsay challenges the assumption that venture funding should be every founder's aim, suggesting that many ideas can flourish through alternative funding and growth models that don't require the massive scale venture investors typically demand.

Timestamp: [27:56-29:58]

• Fundraising experiences can dramatically reverse—from facing universal rejection to navigating bidding wars—once a startup demonstrates traction
• The COVID-19 pandemic forced community-based businesses to either adapt rapidly or fail—Chief's successful pivot to digital ultimately accelerated their national expansion
• Rapid growth can temporarily mask underlying operational problems that eventually resurface as more significant challenges
• Chief survived when similar space-based community businesses failed (like The Wing and WeWork) by meeting executives' heightened need for connection during isolation
• Startup agility provides a crucial advantage during crises—the ability to pivot quickly when larger organizations cannot change course in time
• Successful businesses often require both mission-driven purpose (Chief's goal of supporting women executives) and personal drive (Lindsay's "competitive anger")
• Many entrepreneurs share similar personality traits: desire for autonomy, comfort with challenging norms, and drive to enter spaces where they're "not supposed to be"
• Women founders are often advised to be more aggressive in fundraising and "raise more money" than they might initially feel comfortable seeking
• Founders must distinguish between ideas they personally love and ideas that make viable businesses—not every good concept is a "VC-sized business"
• Personal life events (like pregnancy) often coincide with professional milestones in an entrepreneur's journey, adding additional complexity to the startup experience

Timestamp: [20:00-29:58]

Companies/Organizations:

• Chief - Lindsay's executive network for women that survived the pandemic
• The Wing - Women's co-working space that went under during the pandemic, mentioned as contrast to Chief's survival
• WeWork - Co-working company that faced significant difficulties during the pandemic
• Andreessen Horowitz - Venture capital firm mentioned in the fundraising story

Funding Concepts:

• Series A - Funding round that resulted in a bidding war for Chief
• VC-sized business - Concept discussed regarding whether all startups are suitable for venture capital

Business Approaches:

• Digital pivot - Chief's strategy to survive the pandemic by moving operations online
• National expansion - Accelerated growth strategy Chief implemented after going digital
• Employer spending - Post-panic pandemic trend that benefited Chief as companies focused on executive retention

Metaphors/Analogies:

• Tsunami - How Lindsay described the pandemic's impact on businesses
• Ship vs. kayak - Analogy comparing the agility of startups versus large corporations

Time Periods:

• 2019 - Year of Chief's launch and initial growth
• January 2020 - When Chief closed on expensive real estate deals, just before the pandemic
• 2020 - The pandemic year that forced Chief to completely pivot its business model

Timestamp: [20:00-29:58]

Expanding on her advice about business viability, Lindsay emphasizes that venture capital funding isn't the appropriate path for every startup, despite its prominence in entrepreneurial narratives.

"You don't always have to—there are many situations you should never raise VC. VC is not the right form of money if you don't see yourself being a billion-dollar company that's going to get acquired by Salesforce or go public."

This insight challenges the common assumption that securing venture funding is the default success metric for startups. Lindsay articulates a clear threshold for when venture capital makes sense—primarily for businesses with genuine potential to reach billion-dollar valuations and clear exit paths through acquisition or IPO.

She encourages founders to consider whether their business model truly aligns with the scale and growth expectations of venture investors. Many successful businesses can thrive through alternative funding mechanisms more suited to their growth trajectory and end goals.

However, she reiterates her earlier advice for those who do determine that venture capital is the appropriate path: "If you do want to raise VC, go out, be bold, and raise more."

This balanced perspective—acknowledging both when to pursue venture funding aggressively and when to avoid it entirely—provides nuanced guidance for founders at the crucial decision point of how to finance their businesses.

Timestamp: [30:03-30:25]

When asked about her ultimate vision for Chief—where she would like to see the company in the future—Lindsay articulates a clear brand aspiration rather than focusing solely on financial outcomes.

"I would love Chief to be a definitive household name, aspirational brand that stands for what it is to be a successful businesswoman."

This response reveals her focus on building Chief into a recognizable and influential brand with cultural significance beyond just its core membership. She envisions Chief becoming synonymous with female business leadership, much like how certain brands have become shorthand for their entire categories.

Only after articulating this brand vision does Lindsay acknowledge the financial exit possibility, with a light touch: "An IPO sounds really nice." When the interviewer notes that Lindsay didn't directly mention this outcome, she responds playfully: "I didn't say it though, you did. We're manifesting it. It's going on the vision board."

This exchange highlights an important balance for founders—holding ambitious financial goals while remaining primarily focused on the broader impact and significance of what they're building. Lindsay's emphasis on Chief becoming a "definitive" and "aspirational" brand reveals her understanding that lasting companies transcend their immediate business models to represent larger cultural values and aspirations.

The vision centers on Chief becoming the standard-bearer for what it means to be a successful businesswoman—suggesting that Lindsay sees Chief's ultimate purpose as reshaping perceptions and expectations around female leadership rather than simply providing a service or community.

Timestamp: [30:26-31:19]

When asked about something she's particularly proud of or doesn't typically share, Lindsay opens up about the emotional challenges of receiving criticism from Chief's membership base. Her vulnerability reveals a rarely discussed aspect of entrepreneurship—the personal toll of leading an organization, particularly one serving highly accomplished professionals.

"It's a really stressful job. Members give feedback, and these are executive women so they're all smart, and they all think they could do the job—and they could, because they're all smart, amazing executive women, most of which have more experience than I do."

The nature of Chief's membership—comprised of successful executives—creates a uniquely challenging dynamic when it comes to feedback. Lindsay describes receiving critiques that are particularly cutting:

"There are emails where I'm just like, 'Cool, I quit. I'm going to go cry. This is terrible.' It's devastating."

She contrasts this with her previous experience at Casper, where negative feedback about products felt less personal: "When I worked at Casper, they're like, 'This mattress sucks.' Okay... But this is just really—these are executive women. Every piece of feedback is cutting if it's bad."

Despite these challenges, Lindsay shares a profound moment of validation from a recent conference with 800 Chief members:

"The most rewarding thing is... to hear women tell me how much it matters to them and how it has changed their lives. I forget that sometimes because I'm so focused on making things better because the feedback hurts so much and I take it so personally."

This honest reflection highlights the emotional dichotomy founders often face—being simultaneously wounded by criticism while forgetting to fully absorb positive impact. Lindsay's candor about how personally she takes negative feedback, despite leading a highly successful company, offers an important counterbalance to the often sanitized narratives of entrepreneurial journeys.

Timestamp: [31:20-33:06]

During the audience Q&A, Lindsay is asked whether Chief has considered creating opportunities for emerging women managers—those with high potential but not yet at the executive level, such as recent MBA graduates or those earlier in their leadership journeys.

Lindsay's response reveals her broader vision for Chief as potentially developing into a portfolio of communities serving women at different career stages:

"I big picture think of Chief as it could build into a portfolio company where Chief represents 'chief'—it was obviously named because of Chief Executive Officer, Chief Financial Officer—but there could be and should be other communities down the road."

This strategic thinking aligns with her earlier stated mission of building an "aspirational brand that stands for successful women in business." She acknowledges that executive titles aren't the only measure of success:

"You don't have to be at the executive table to be a successful, influential business person."

However, Lindsay demonstrates disciplined prioritization by emphasizing that Chief needs to perfect its core offering before expanding to new segments:

"What we want to accomplish first though is perfecting the product. As I mentioned, we've never really had a great normal year of business, and so I think us figuring out the perfect product—where some of it's digital, some of it's in person, how she's maximizing her time and spend with us—we want to nail that and get that right before we start building out other communities."

This answer highlights Lindsay's strategic approach to growth—focusing on excellence in their current offering before expanding, while still acknowledging the clear opportunity to serve a broader audience of women leaders at various career stages in the future.

Timestamp: [33:07-34:48]

An audience member who has visited Chief spaces asks about the intentionality behind Chief's branding and community-building approach, specifically referencing the distinctive green color used throughout their spaces (and a rumor about Benjamin Moore potentially naming a paint color "Chief green").

Lindsay confirms that while the paint color naming hasn't happened yet, the brand's design choices were indeed highly strategic. She explains that Chief's distinctive green color was a deliberate departure from gendered color schemes common in women-focused spaces:

"The Wing was all the rage—it was very pink. And then I think people thought like the opposite of pink would be blue. We wanted to find something that was gender neutral because we didn't want to create Chief as a space that alienated men."

This decision reflects a fundamental value in Chief's approach to supporting women executives:

"It wasn't about that—we are not anti-men. Our investors are men. We have men that come into Chief all the time. So we wanted to actually choose the color and choose design and words that were thoughtful around how women felt comfortable without alienating anybody else. To make you feel included did not mean excluding others."

Lindsay also reveals an interesting early decision regarding their visual identity—they deliberately avoided showing images of women on their website for years:

"We specifically did not want to show any photos of women, and we didn't for years. Only recently we finally added photos for conversion because pictures of women convert better—I lost that battle with my marketing team."

The reasoning behind this choice reflected a deep understanding of the psychology of their target audience:

"We didn't want photos of women because I didn't want someone to see a woman and think like, 'Oh, I look like... I'm too young or I'm too old or that woman looks too skinny.' I just wanted somebody to see the words about power and having a seat at the table and feeling like they related, not necessarily as women."

Lindsay notes that women are "constantly slammed with photos of other women," often creating unintentional barriers through comparison. She personally experiences this phenomenon:

"When I think about powerful women, I don't see myself. I see like Cheryl Sandberg. I see Oprah. I see women who don't look like me. And I think there's an impostor syndrome that many women carry."

This thoughtful approach to visual identity—focusing on the concept and value proposition rather than visual representation—highlights the careful consideration behind Chief's brand development.

Timestamp: [34:49-39:18]

• Venture capital isn't appropriate for all businesses—only pursue it if you realistically see your company reaching billion-dollar valuation or exiting via acquisition/IPO
• Having a clear brand vision that transcends financial outcomes helps guide long-term company development
• Building a community for high-achieving professionals creates unique challenges—members are often highly critical and believe they could run the business better
• Founders often focus disproportionately on negative feedback while undervaluing the positive impact they're creating
• Successful companies can evolve into portfolio businesses serving different segments, but focus on perfecting your core offering before expanding
• Brand decisions should align with deeper values—Chief chose gender-neutral green to create an inclusive environment that didn't alienate men while still focusing on women
• Visual representation matters—Chief initially avoided showing images of women to prevent impostor syndrome and comparison barriers
• Intentional design choices can help address psychological barriers like impostor syndrome that might prevent potential members from engaging
• Creating inclusive spaces for underrepresented groups doesn't require excluding others—effective communities can welcome allies
• Long-term vision requires balancing aspirational goals (being a household name) with pragmatic business outcomes (like IPO)

Timestamp: [30:03-39:58]

Companies/Organizations:

• Chief - Lindsay's executive network for women
• Salesforce - Mentioned as a potential acquirer for venture-backed companies
• Casper - Lindsay's previous company, referenced when discussing customer feedback
• The Wing - Women's co-working space mentioned as using pink in their branding
• Benjamin Moore - Paint company referenced in a question about potentially naming a color "Chief green"

People:

• Cheryl Sandberg - Referenced as an example of a powerful woman leader who creates comparison challenges
• Oprah - Referenced as an example of a powerful woman who doesn't resemble most women in business

Concepts/Terms:

• IPO (Initial Public Offering) - Mentioned as a potential future outcome for Chief
• Portfolio company - How Lindsay envisions Chief potentially expanding to serve different segments
• Impostor syndrome - Psychological barrier mentioned as affecting women in leadership
• Conversion - Marketing concept referenced regarding website design choices

Design Elements:

• Green color - Chief's intentional branding choice to create a gender-neutral environment
• Photo-free website - Chief's early design choice to avoid showing images of women to prevent comparison

Roles/Titles:

• Chief Executive Officer - Referenced regarding the origin of the company name
• Chief Financial Officer - Referenced regarding the origin of the company name
• Emerging managers - Potential future audience for Chief's expanded offerings

Timestamp: [30:03-39:58]

Responding to a question about how Chief translated their concept into a product people would pay $7,000 annually for, Lindsay explains how they built their core offering by studying what made existing successful networks so "retentive" for members.

"We modeled our core service on what we discovered made YPO so retentive for their members. As I said, there's no new ideas, there's very few new ideas."

Chief's central product concept was inspired by YPO's "forum" model—small peer groups that create both value and social accountability:

"YPO was built on this idea of forum, which is 10-person peer groups. And if you find a great group and you love it, there's kind of a peer pressure that you show up every month for your group. You have these intimate conversations."

This small-group format became Chief's foundational offering, differentiating it from more generic networking organizations:

"That's actually the core product of Chief. You are not just signing up for this generic network with events. You are signing up and we are curating you into a group of 10 other executives who are at your level, who we have determined would be a great fit for you."

This curation process—matching executives with compatible peers—proved to be a compelling value proposition for their target market. As Lindsay notes, "for many executives we spoke to, that was the selling point."

However, scaling this high-touch model presented significant operational challenges. What worked easily with 50 members became increasingly complex with hundreds:

"It was easier because we had a bigger N, so we had more people that allowed us to curate into more defined groups, but it's significantly harder to start curating hundreds of women into cohorts instead of 50. Fifty was like putting together wedding tables—'move her here, move her here.' Once you have hundreds... we had to start figuring out, for us, building an algorithm around size of team, where somebody worked, seniority level, zip code."

Lindsay credits venture capital funding with enabling them to develop the technology needed to scale this personalized curation process to serve a much larger membership base.

Timestamp: [40:05-42:11]

When asked whether technology was the primary enabler of Chief's scale, Lindsay offers a nuanced perspective on what truly drove the company's growth and retention. She distinguishes between operational enablement and true business drivers:

"I think we are a tech-enabled company, and there is an emotional factor to wanting to stay that has nothing to do with the technology."

This insight reveals an important distinction that many founders miss—technology can facilitate operations and enable scale, but it doesn't necessarily create the emotional connection that drives customer acquisition and retention:

"The tech allows us to operate, and it helped fuel the growth, but it is not the cause of growth. I believe it was the brand, the movement, the word of mouth that allowed us to scale and retain members."

Lindsay's perspective highlights that while Chief needed technology to manage its expanding membership base and facilitate sophisticated matching of members into compatible groups, the fundamental value proposition and emotional connection came from elsewhere.

This distinction is particularly relevant for community-based businesses, where operational technology can enable growth but doesn't itself create the sense of belonging that makes members want to join and stay. The true drivers—brand identity, community feeling, and member experiences—generate the word-of-mouth that fuels organic growth.

This balance between technological enablement and emotional connection represents a sophisticated understanding of how different elements contribute to a company's success, particularly for membership-based business models.

Timestamp: [42:12-43:04]

Asked about what she learned from her experience at Casper that she applied to Chief, Lindsay highlights both positive lessons she carried forward and practices she deliberately left behind.

Her most significant takeaway was the importance of building an exceptional team with distinctive personalities:

"I learned at Casper about the power of hiring people that are amazing and quirky and weird. Casper had some of the weirdest, most talented, phenomenal people that I'm still friends with, that I love—the founders, the early team."

Lindsay emphasizes that these early hires play an outsized role in a startup's trajectory:

"Those early teammates are so important to the success and growth of an early startup because each person's wearing 12 hats. If there's drama—I mean, who has time for drama? You're building a business."

However, she also identified spending patterns at Casper that she deliberately avoided replicating at Chief:

"Something I learned that I didn't bring with me was—I think it was a different era of spend—but we spent a lot of money on company parties and big, silly marketing initiatives that were good for brand. But I look back and I'm like, 'Oh my God, we just burned through some money.'"

This reflection influenced her approach to financial discipline as a founder:

"As a founder, I am a lot stingier about spend and wanting to build culture without necessarily needing to throw an annual party at NOBU."

This balance—embracing the people-centric aspects of Casper's culture while adopting a more disciplined approach to spending—reflects Lindsay's evolution as a leader and her deliberate choices about which practices to carry forward into her own company.

Timestamp: [43:05-44:38]

When asked about a strongly held belief she's recently changed her mind about, Lindsay initially struggles to identify a specific example. However, her response reveals an important leadership philosophy about flexibility and decisiveness:

"I change my mind all the time, and I think people who start working with me are surprised by it because I come in so passionately strong, and the second I get new information, I will change my mind."

This willingness to pivot based on new information, despite initially presenting strong convictions, represents an approach to leadership that balances confidence with adaptability. She continues:

"I do like to operate both passionately and strongly and stubbornly, but also I think it's important to have the openness and curiosity and willingness to be wrong."

What's particularly insightful is Lindsay's recognition that this flexibility is actually a privilege that comes with her position:

"I often tell my team it's the luxury and the privilege of being the founder, which is like, 'Oh, I've changed my mind.' It's hard to do that when you are working because you are lobbying for your team, you are trying to be the champion of your domain, in your silo, and so you can't look like you got it wrong. You almost feel like you have to continue down that bet."

This observation highlights a real dynamic in organizational politics—middle managers and team leads often feel pressure to remain consistent and defend their positions, while founders can more freely change direction without losing face or authority:

"It's a luxury that I change my mind a lot, that I acknowledge and think is a privilege of being the boss."

This candid reflection on the power dynamics of decision-making and the ability to change course offers insight into how founder authority operates differently from other leadership roles, and how Lindsay consciously navigates this privilege.

Timestamp: [44:39-46:15]

Responding to a question about balancing growth with exclusivity, Lindsay articulates a fundamental tension that many premium membership organizations face—how to maintain exclusivity while also growing and being inclusive.

She begins by noting that Chief's target market naturally expands as women advance in their careers:

"When I think about what Chief today stands for, we are looking at executive women, and there are new executive women who are stepping into those levels every day. Every day women are getting promoted."

This creates a natural pipeline of potential members who meet their criteria. Chief maintains a waitlist of women who have applied but don't currently meet their membership requirements, maintaining contact with them for potential future membership:

"We have a waitlist of women who have applied to Chief who are not technically at the criteria we would accept them, and we go back through that list. We often correspond with members or potential new members who can then join Chief later."

However, Lindsay acknowledges the core paradox they face:

"It's a really interesting tension because you don't want Chief to get too big because then it's no longer exclusive, but we do also want to grow."

This is where her concept of potentially creating different communities for different career stages becomes relevant again—allowing growth without diluting the core value proposition.

She candidly addresses the cultural complexity of building an exclusive organization in today's social climate:

"I also think there's a challenge there of being exclusive, especially today in a society that has qualms with exclusivity. And like, there's a reason there are inclusivity teams. So how do you build exclusivity but then also do it on a foundation of community inclusivity? How do you have exclusivity-inclusivity at the same time? That is a challenge, and it's nuanced."

Lindsay acknowledges that this approach inevitably creates disappointment for some:

"We have people who apply for Chief that don't get in that absolutely hate us, and I think it's one of the problems that I want to solve through other communities and other cohorts."

This thoughtful reflection on managing the contradiction between exclusivity and inclusivity reveals the complex considerations involved in building a premium network that derives part of its value from selective membership while operating in a social context that increasingly values inclusivity.

Timestamp: [46:16-48:20]

An audience member who had previously encountered Chief shared an observation about the company's early branding, noting a tagline that resonated with her: "It's not what you are, but it's who you know." She connected this to research suggesting different relationship-building patterns between genders:

"There's a saying that women become friends face-to-face, and men become friends shoulder-to-shoulder."

She appreciated how Chief's branding seemed to transcend traditional gender divisions:

"Hearing you say that you wanted this green color and Chief to be separate from like boys blue, girls pink situation—it was not about what you are necessarily, but it was about how you can help this collective."

This observation leads to a revealing moment about how Lindsay has evolved in her thinking, as another audience member points out:

"An example when you changed your mind—actually the landing page. You were resistant on it for a while, and then they changed your mind because the conversion rate went up."

This example effectively illustrates Lindsay's earlier point about being willing to change direction based on data, despite strong initial convictions. It shows how her principle of being "passionately strong" but open to changing her mind materializes in practical business decisions.

The question then shifts to whether Chief's early marketing had different appeals to women executives who were mothers versus those who weren't. This prompts Lindsay to reflect on the diverse personal circumstances of Chief's leadership team:

"It's interesting—my co-founder is not married and doesn't have kids. I am married, I had a kid, and then as you found out, had another."

This exchange highlights how Chief has navigated gender dynamics in its branding—seeking to create a brand identity that speaks to professional women regardless of their personal circumstances while being responsive to data about what resonates most effectively with their target audience.

Timestamp: [48:21-49:54]

• Successful business models often build on proven formats—Chief adapted YPO's "forum" model of 10-person peer groups rather than inventing a completely new structure
• The core product offering that justified Chief's premium price was carefully curated peer groups of compatible executives, not just generic networking access
• Technology enables operations and scale but doesn't necessarily drive growth—Chief's success stemmed more from brand strength and emotional connection than its tech platform
• Early hiring decisions are critical for startups—finding "amazing, quirky, weird" people who can wear multiple hats creates the foundation for success
• Financial discipline differs across startup eras—Lindsay adopted a more conservative approach to spending at Chief compared to earlier experiences at Casper
• Founders have the "privilege" of changing their minds more freely than other leaders in an organization, who often feel pressure to defend initial positions
• Premium membership businesses face an inherent tension between maintaining exclusivity (which creates value) and pursuing growth (which can dilute exclusivity)
• Creating an exclusive community while respecting modern values of inclusivity presents a nuanced challenge that requires careful positioning
• Gender dynamics in professional networking often differ (face-to-face vs. shoulder-to-shoulder), influencing how Chief designed its community experience
• Data-driven decision making (like conversion metrics) can help resolve branding debates, demonstrating the value of being open to changing direction when evidence supports it

Timestamp: [40:05-49:54]

Organizations/Networks:

• Chief - Lindsay's executive network for women
• YPO (Young Presidents' Organization) - Executive network whose "forum" model inspired Chief's core product
• Casper - Company where Lindsay worked previously and learned key lessons about team building and spending

Business Concepts:

• Forum model - 10-person peer groups that provide accountability and intimate conversation, borrowed from YPO
• Tech-enabled company - How Lindsay describes Chief—using technology to operate but not being fundamentally a tech company
• Conversion rate - Metric mentioned regarding website changes and including photos of women

Places/Venues:

• NOBU - High-end restaurant mentioned as a place where Casper would hold expensive company parties

Relationships/Dynamics:

• "Women become friends face-to-face, men become friends shoulder-to-shoulder" - Saying referenced about different relationship-building patterns
• Wedding tables - Metaphor used to describe the early member curation process

Business Challenges:

• Exclusivity-inclusivity paradox - The tension between maintaining selective membership while respecting inclusive values
• Algorithm development - Process Chief created to scale member curation based on factors like team size, location, and seniority

Marketing Elements:

• "It's not what you are, but it's who you know" - Early Chief tagline mentioned by an audience member
• Landing page evolution - Example given of Lindsay changing her mind based on conversion data

Timestamp: [40:05-49:54]

Responding to the earlier question about whether Chief's marketing specifically targeted executive mothers, Lindsay reveals an important principle about product focus that guided their decision-making.

"When we try to serve too many needs, we do a really terrible job serving the need that we promised, which is you're joining Chief because you are an executive and because it's lonely at the top."

This insight reflects a common challenge for growing companies—the temptation to expand services to address every customer need, potentially diluting the core value proposition. Lindsay emphasizes that Chief's primary focus remains on executive challenges:

"You are dealing with problems like people problems at work and managing the board and layoffs and severance and DEI issues."

While parenting challenges might naturally arise in member discussions, Lindsay explains that Chief deliberately avoids positioning itself as a parenting resource:

"We're not the experts in parenting. It's something that we would then try to find a partner with."

This strategic restraint comes from a clear understanding of their organizational competencies:

"We've learned that we kind of have to stick to what we know, which is executive stuff, and be the master of just that domain and not spread ourselves too thin."

This disciplined approach to product focus—identifying what the company does exceptionally well and deliberately avoiding expansion into tangential areas—represents a crucial strategic decision that has helped Chief maintain clarity in its value proposition and market positioning.

Timestamp: [50:03-51:05]

When asked how to convince founders who are reluctant to raise money because they fear losing control of their companies, Lindsay offers a bluntly realistic perspective on competitive dynamics in startups.

She begins by challenging the viability of a "slow and steady" approach to growth:

"I don't love slow and steady because I don't believe there are new ideas, which means chances are whatever you're working on, 10 other people are working on it."

This perspective builds on her earlier point about innovation often coming from repurposing existing ideas rather than inventing entirely new concepts. In this competitive reality, she argues that speed becomes a crucial advantage:

"Somebody else is going to raise that money, move faster, start hiring, start advertising, and they will eat you for lunch. That's the story that I tell somebody that I'm advising."

Lindsay frames fundraising not as an optional path but as a competitive necessity in many cases:

"I know somebody else in this space. Do you think that they're being protective? Do you think they want to move slow? Go out and raise the money, or they will raise the money first. You need a war chest."

She particularly emphasizes the threat posed by unknown competitors—those operating in stealth or who haven't yet appeared on the radar:

"When you're working, you often don't know of your competitors. There are the ones you know, and there are competitors out there you don't know, and those are the ones that are the scariest—the known knowns and then the unknown unknowns."

This stark competitive framing provides a compelling counterargument to founders' concerns about dilution—suggesting that maintaining larger ownership of a company that gets outcompeted is ultimately less valuable than having a smaller percentage of a company positioned to win.

Timestamp: [51:06-53:30]

When asked whether investors dismissed Chief as targeting a "niche market" due to its focus on women executives, Lindsay shares how they countered this perception with concrete data and compelling comparisons.

Their approach started with gathering quantifiable market size information:

"We got the numbers from LinkedIn. We just pulled up the TAM (Total Addressable Market). There are five million women in the US alone who identify themselves on LinkedIn that would fit into the criteria of Chief."

This data-driven approach helped counter uninformed assumptions about market size. Lindsay notes with some frustration a common response from male investors:

"Almost every investor was like, 'Let me go ask my wife if she would join this,' which is like, man, really?"

Beyond raw market size data, Lindsay emphasizes the importance of identifying comparable businesses ("comps") that have achieved significant scale or exits. This approach demonstrates that similar business models have already proven viable for venture-scale returns:

"I don't feel like you guys are all really sophisticated, and maybe I'm saying something you already know, but having great comps around other businesses that are same but different, that have clearly reached VC size, that have had amazing exits or huge revenue numbers—show that it could be done."

For Chief, this meant highlighting successful membership organizations serving executives:

"We showed YPO is a nonprofit and it's huge. Vistage had been acquired multiple times by private equity."

With market size data and successful comparables established, Lindsay frames the investment decision as a straightforward equation:

"It's just a math equation. Showing these big businesses, showing our TAM, it's like the easiest math in the world that if we can execute—and we got two startup pros that can execute—1+1 equals big exit."

This comprehensive approach to market sizing and validation provides a template for founders facing similar objections about addressable market concerns, particularly for businesses targeting underserved demographics.

Timestamp: [53:31-55:51]

An audience member shares her experience considering a "women in AI" podcast and receiving feedback from female AI researchers who didn't want to be tagged specifically as "women researchers." This prompts Lindsay to address the complex tension between creating identity-specific spaces while avoiding tokenization.

"It's tokenization, right? Like nobody wants to feel like they are the token. I don't want to be a 'woman founder'—I'm a founder. Like, I can go toe-to-toe with any founder, doesn't matter what sex or gender I am."

This resistance to being defined primarily by gender rather than professional accomplishments is a common sentiment among high-achieving women. However, Lindsay immediately acknowledges the paradox this creates:

"But we also still want to promote... It's a double-edged sword, right? There is a fine line between creating inclusive spaces and making sure that we can be a champion for one another, without feeling like we are being tokenized."

She points to the harmful impact of reductive thinking that diminishes accomplishments by attributing them to diversity considerations:

"When people said that like Kamala is a diversity hire—that's so insulting, it's terrible."

Lindsay then shares the internal experience many women face in professional settings:

"Any time a woman's in the room, there's always a little thought in her head that she's like, 'Not only am I the only woman in the room, did they just invite me so they have a woman in the room?'"

Her advice ultimately encourages moving forward despite these concerns:

"But you know what? Who cares—I'm in the room, so I'm gonna be in the room. I know I'm smart. So do your podcast! People talk about everything, right? I would just say you're thinking about the thing that's worrying you more than anybody else."

Lindsay concludes with a personal reflection that encapsulates this nuanced position:

"I'm a woman founder today. I wasn't invited here to be a woman founder, but the conversation naturally got here. And people like to label and tokenize—prove them wrong."

This thoughtful examination of the tokenization paradox offers guidance for navigating the complex reality of creating identity-specific spaces while maintaining professional dignity and avoiding reductionist perceptions.

Timestamp: [55:52-58:46]

In the final question of the session, Lindsay is asked to reflect on what makes an effective pitch deck, drawing from both her experience as a founder and her current perspective as an investor. Her response emphasizes balancing analytical and emotional elements.

She identifies three key components investors are evaluating:

"When I look at a founder, I am looking at: Do I believe in this as a product? Do I believe that you are the person to execute this? And do I believe that this could be a billion-dollar, VC-viable size business?"

Lindsay stresses that these elements need to be woven together through effective storytelling:

"I want to see that relationship tied together in a great story."

While financial expertise matters, she emphasizes that early-stage pitches require a compelling narrative:

"Early stage is both some of the numbers—like I really want to believe that you have the financial expertise, or your team member does—but there's a bit of storytelling there."

This insight connects to her earlier point about founders needing to be both product builders and storytellers:

"At the end of the day, as a founder, you are a storyteller—to investors, to customers, to team. And if you can't tell a great story in that pitch deck that inspires me and convinces me, that mix of emotion and logic..."

Lindsay admits that her own early pitch decks may have lacked this balance:

"I don't know if my early pitch deck had it. It was ugly. It was so ugly. It was not yet green—I didn't know yet."

When asked what she would have done differently with her early pitch material, Lindsay highlights the importance of narrative cohesion:

"I would weave together a better narrative that hopefully would have avoided 99 NOs that sounds like we both received, because I think it felt choppy. And I don't know how convincing we were that we were the right people to take that small investment and build and execute a product that could get to that next valuation."

This focus on creating a cohesive narrative that blends analytical evidence with emotional resonance provides valuable guidance for founders crafting their fundraising presentations.

Timestamp: [58:47-1:01:03]

As the session concludes, Lindsay shares information about her current investment activities, revealing her dual investment approaches:

"For anyone who is interested in Chief, check it out. And if you're early stage and looking... feel free to email me. I invest out of Next Wave NYC, so we have an investing thesis around AI."

Beyond her institutional investing work, she also makes personal angel investments with a different focus:

"And then I also, on my own, angel invest—more consumer-facing. And I have a mild focus on, but not exclusively on, women."

This brief insight into Lindsay's investment activities demonstrates how her experiences as a founder have influenced her transition to the investor side of the table. She maintains a commitment to supporting women founders, but notably doesn't limit her investments exclusively to female-led companies—reflecting her earlier comments about the complex balance between creating targeted support while avoiding tokenization.

Her investment in AI-focused startups through Next Wave NYC also shows her engagement with emerging technologies, while her personal angel investments in consumer-facing businesses leverage her extensive background in brand-building and consumer marketing.

Timestamp: [1:01:04-1:01:58]

• Focus is crucial for startups—attempting to serve too many needs simultaneously undermines the core value proposition
• Startups should "stick to what they know" and be "master of just that domain" rather than spreading themselves too thin
• In competitive markets, "slow and steady" growth is often not viable—when multiple teams are working on similar ideas, the best-funded often win
• Founders who hesitate to raise capital out of fear of dilution may ultimately lose to competitors who secure a "war chest" for rapid scaling
• Unknown competitors ("unknown unknowns") pose a greater threat than visible ones—making defensive fundraising a strategic necessity
• Market size objections for underrepresented demographics can be countered with concrete data—Chief identified 5 million potential members through LinkedIn
• Comparable businesses ("comps") that have achieved successful exits provide powerful evidence for investors questioning market size
• Founders building identity-focused spaces face the "tokenization paradox"—balancing the benefits of targeted communities against the risk of limiting perceptions
• Effective pitch decks balance analytical evidence with emotional appeal—"that mix of emotion and logic"
• A compelling narrative that ties together product, team, and market opportunity is often what early pitch decks lack
• Financial expertise matters, but storytelling skills ultimately determine fundraising success in early-stage ventures
• Some founders transition to investing after successful exits, bringing practical experience to their investment decisions

Timestamp: [50:03-1:01:58]

Organizations/Networks:

• Chief - Lindsay's executive network for women
• YPO (Young Presidents' Organization) - Nonprofit executive network mentioned as a comparable business
• Vistage - Executive coaching organization referenced as having been acquired multiple times by private equity
• Next Wave NYC - Investment firm where Lindsay invests with a focus on AI

Business Concepts:

• TAM (Total Addressable Market) - Concept discussed in addressing "niche market" concerns
• War chest - Term used to describe the funding necessary to compete effectively
• Comps (Comparable companies) - Referenced as important for demonstrating market viability
• Tokenization - Concept discussed regarding identity-specific spaces and communities

People:

• Kamala Harris - Referenced in discussion about harmful "diversity hire" narratives

Books/Resources:

• "Only the Paranoid Survive" - Book mentioned by audience member in relation to competitive vigilance

Industry Challenges:

• DEI (Diversity, Equity, and Inclusion) - Mentioned as one of the executive challenges Chief members face
• "Women in AI" - Example used by audience member regarding tokenization concerns
• Board management - Executive challenge mentioned as part of Chief's focus
• Layoffs and severance - Executive challenges mentioned as part of Chief's focus

Investor Psychology:

• "Known knowns" and "unknown unknowns" - Terms used to describe different levels of competitive awareness
• Logic and emotion in pitch decks - Framework described for effective fundraising presentations

Timestamp: [50:03-1:01:58]