When Should You Trust Your Gut?

In this episode of Dalton & Michael, the hosts explore a crucial dilemma that startup founders face: when should you trust your gut instinct versus when should you seek validation from others?

The hosts identify two common founder scenarios they encounter at Y Combinator. One involves experienced founders who've already built something valuable and want to turn it into a product. The other involves inexperienced founders who are trying to figure out what to work on.

As the hosts point out, general startup advice doesn't apply equally well to these different scenarios - each requires a more tailored approach based on the founder's background and expertise level.

The hosts outline the two extreme approaches that founders sometimes take when deciding whether to trust their instincts.

On one end is the "Steve Jobs approach" - founders who believe they should never talk to customers and instead rely completely on their vision and taste to create revolutionary products that people didn't even know they wanted.

On the opposite end is what the hosts call "the mom test" approach - founders who assume they know absolutely nothing and must rely entirely on customer feedback to guide every decision, having no opinions of their own.

The hosts note that they sometimes encounter founders who say, "We don't know what to work on so our plan is to talk to people and they'll tell us what to work on," which represents the 0% trust-your-gut approach.

The hosts argue that founders with relevant expertise should trust their instincts more than they might think.

If you've built something valuable at a company that's still being used even after you've left, or you've developed a successful product in a particular domain, you've likely developed taste and understanding that gives you unique insights others don't have.

For these founders, Michael suggests a simple approach: "Make something that would impress you." When you have deep expertise in a domain - even if it's something arcane like building compilers - your ability to judge quality and discern what's valuable is a superpower.

The hosts note that as advisors, their job with these founders isn't to have opinions but to encourage them to trust their experience: "Would you have liked this? Would you have bought it? Would you have talked to yourself?"

The hosts explain that you might want to be more cautious about trusting your instincts when:

1. You don't have many strong opinions about what to work on
2. Your opinions are mainstream or similar to the "50th percentile" of other people
3. You've never gone deep on any particular topic
4. You haven't had many relevant experiences

In these situations, the hosts suggest a different mentality: part of starting your company will be about building expertise, not bringing it. They recommend:

1. Starting in a general idea area that interests you
2. Not over-complicating your initial plan
3. Giving yourself the opportunity to learn and figure things out

The hosts emphasize they're not saying one path (having expertise vs. building it) is better than the other - they're just encouraging founders to be self-aware about which category they fall into and implement a plan accordingly.

To illustrate their points, the hosts walk through a concrete example: two different founding teams both wanting to create a real estate software company focused on mortgage underwriting.

Example #1: The Experienced Team

In the first scenario, one founder has 10 years of experience as a real estate agent, or one founder worked at a mortgage underwriting company for a decade and built software for that industry.

This team likely has:

• Deep industry knowledge
• Experience with existing products and their limitations
• Understanding of what mortgage underwriters actually want
• Firsthand experience with the problems they're solving

For this team, trusting their gut about what to build makes sense because they're speaking from experience.

Example #2: The Inexperienced Team

In the second scenario, the founders have no industry experience beyond perhaps having bought a house themselves. They believe the real estate industry is "broken" and they can "fix it," but they haven't done research or talked to industry professionals.

This team would benefit from starting with a simpler approach, talking to people in the industry, and building expertise along the way rather than assuming they already know the solution.

The hosts identify a pattern where founders often operate in ways misaligned with their experience levels:

When Experts Act Like Novices

Experienced founders sometimes doubt their expertise and undervalue their insights:

Another common mistake is when founders know exactly what the market needs but try to add buzzwords like AI to make their startup seem more "fundable":

When Novices Act Like Experts

Meanwhile, inexperienced founders sometimes overplan as if they already have deep expertise:

These founders would benefit from building the smallest possible solution and learning as they go, rather than assuming they already know exactly what needs to be built.

The hosts emphasize that their advice isn't about having a universal "right way" to approach startup building. Instead, founders should adapt their approach based on their expertise level:

If you have expertise:

• Trust your instincts more
• Build something that would impress yourself
• Don't feel the need to add buzzwords to make your idea seem more "fundable"
• Use your domain knowledge as a competitive advantage

If you're building expertise:

• Keep your initial solution simple
• Be open to learning and adapting
• Choose an area you're genuinely excited to learn about
• Don't commit to complicated, long-term plans upfront

The hosts conclude by noting the value of personalized advice:

• One-size-fits-all startup advice doesn't work - your approach should be tailored to your specific background and expertise level.

• Founders with deep domain expertise should trust their instincts more and build products that would impress themselves.

• Founders without relevant experience should be more cautious about assuming they know what to build and should focus on learning quickly.

• A common mistake is when experienced founders doubt their expertise, while inexperienced founders over-plan as if they already know everything.

• If you lack domain expertise, choose to work in an area you're genuinely excited to learn about, as you'll need to build that expertise along the way.

• Building "what impresses you" is good advice for experts because they have the taste and judgment to discern quality in their domain.

• Don't add buzzwords like "AI" to your product just to make it seem more fundable if that's not actually what solves the problem.

• For inexperienced founders, starting with a simple solution and learning from real users is more effective than extensive planning based on market reports.