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Why Most Founders Chase the Wrong Ideas

Strategy
July 8, 2025
Andrew Wilkinson shares lessons from building 75+ businesses without VC.
Topics discussed in the episode:
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How can startups avoid entering markets dominated by large competitors?
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Why is it important to hire for fit rather than potential you hope to develop?
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What skills should founders and employees focus on in the age of AI?
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How can founders ensure they hire CEOs aligned with their company's direction?
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What is the importance of hiring the right people in a startup?
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What impact will AI have on knowledge work jobs in the near future?
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How can founders use AI agents to automate personal workflows?
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How can founders leverage their passions to build profitable businesses?
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Why should founders consider boring or less competitive markets?
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What is your best advice for coming up with a great startup idea?

How can startups avoid entering markets dominated by large competitors?

Strategic market selection helps startups thrive.

"You don't want to be fighting against the commercial fishermen... find the other fishing hole, don't go where the trawlers are."

  • Avoid markets dominated by large competitors.
  • Seek niches where your startup can stand out.
  • Focus on areas with less competition.

Why is it important to hire for fit rather than potential you hope to develop?

Effective hiring focuses on current fit over potential change.

"I've just found that the biggest mistake I made in my early career was I would hire people because I liked them on gut, and I would think that I could change them."

  • Hire individuals who already meet your needs.
  • Avoid expecting to change employees significantly.
  • Focus on immediate alignment with goals.

What skills should founders and employees focus on in the age of AI?

Adapting to new technology is key for founders in the AI era.

"I feel like coding has really gone away because of that, and I think now people are saying people need to learn how to prompt, which I think is very true for the tool set right now."

  • Embrace AI tools and learn prompt engineering.
  • Continuously adapt to technological changes.
  • Utilize AI to enhance productivity.

How can founders ensure they hire CEOs aligned with their company's direction?

Selecting leadership that aligns with company vision is vital.

"Listening incredibly carefully to people's words and their experiences because generally people will do the thing they tell you."

  • Note if candidates' strategies match your expectations.
  • Hire leaders who naturally align with your goals.
  • Avoid trying to change a leader's approach.

What is the importance of hiring the right people in a startup?

Effective team building is essential for startup success.

"My business partner Chris has a really great quote. He says, there are no problems, there's only people problems."

  • Hiring the right people solves most business issues.
  • Avoid keeping difficult team members.
  • Build a team that aligns with your values.

What impact will AI have on knowledge work jobs in the near future?

Understanding AI's impact on employment is crucial for founders planning team building.

"So many knowledge work jobs are going to change massively... I think the fundamental question is, do all jobs just become a single prompt."

  • AI may automate many knowledge-based tasks.
  • Founders should anticipate changes in workforce needs.
  • Embrace AI tools to stay competitive.

How can founders use AI agents to automate personal workflows?

Utilizing AI agents can help founders streamline tasks and improve productivity.

"And then next time I travel to the Bay Area, the agent will see two weeks before and it'll say, I saw you're going to San Francisco. Here's all the people in San Francisco you should try and have coffee with."

  • Implement AI agents to automate scheduling.
  • Enhance networking by leveraging AI to track contacts.
  • Save time by automating repetitive tasks.

How can founders leverage their passions to build profitable businesses?

Aligning personal passions with business opportunities helps founders find Product-Market Fit.

"I think often you find your passion, you know your skill set, you zero in and then you just kind of pivot and you find the most profitable way to do it."

  • Identify your unique passions and skills.
  • Adjust your idea to find the profitable niche within your passion.
  • Leverage strengths to create a sustainable business model.

Why should founders consider boring or less competitive markets?

Founders seeking Product-Market Fit should target less crowded markets to increase success.

"He gives this example... if you're a fisherman, and you see a large pond... you actually want to walk off into the forest and find a small fishing hole with lots of fish and very little competition."

  • Target niches with high demand but less competition.
  • Avoid oversaturated markets where everyone is competing.
  • Finding untapped opportunities can lead to greater success.

What is your best advice for coming up with a great startup idea?

Generating a successful startup idea is key to finding Product-Market Fit.

"Charlie Munger... says, fish where the fish are. The biggest mistakes I've made have been going into business models where other people have repeatedly failed and thinking I can do this better."

  • Focus on markets with proven demand.
  • Avoid copying models where others have failed.
  • Use your unique strengths to find less competitive niches.