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From Stalled Startup to $10M ARR in One Year

Finding PMF
June 18, 2025
Jordan Dearsley reveals how his pivot unlocked major AI growth.
Topics discussed in the episode:
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What strategies did you use for distribution and marketing?
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How did you manage customer demands during rapid growth?
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How did you transition from a previous product to finding a new opportunity?
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What advice do you have for founders seeking product-market fit?
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How can startups provide value through last-mile integration?
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How did you compete with big players like OpenAI?
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How did you handle rapid growth with a small team?
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How did you build conviction to persist through challenges?
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How important is it to solve a 10 out of 10 problem for customers?
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How did moving to San Francisco affect your startup's direction?

What strategies did you use for distribution and marketing?

Opening: Effective distribution doesn't always require significant marketing spend. Quote:

"We did zero ads... We did zero marketing... We just have like this Discord community and like maybe some people make YouTube videos about us... That's basically it."

Takeaway:
  • Leverage community engagement for organic growth.
  • Encourage user-generated content to spread awareness.
  • Focus on product quality to drive word-of-mouth promotion.

How did you manage customer demands during rapid growth?

Opening: Rapid growth often leads to increased customer demands that can strain resources. Quote:

"We had to open tons of Slack channels with everyone... It got noisy... We just had like tons of people hounding us for support all the time... We had to close them... We could not focus on what was important."

Takeaway:
  • Establish boundaries to manage customer communication.
  • Prioritize tasks to focus on critical growth areas.
  • Streamline support to maintain productivity.

How did you transition from a previous product to finding a new opportunity?

Opening: Pivoting can lead to discovering new opportunities when a product isn't meeting expectations. Quote:

"We grew to about $50 million in revenue over like 3 years, and we just gave all the money back to all of the users... Then kind of just was waiting around in the darkness for a good 3 or 4 months."

Takeaway:
  • Be willing to let go of products that aren't working.
  • Use downtime to explore and experiment with new ideas.
  • Embrace uncertainty as part of the entrepreneurial journey.

What advice do you have for founders seeking product-market fit?

Opening: Finding product-market fit is often about solving real, pressing problems for customers. Quote:

"Don't think it's a really big thing... You can have product-market fit immediately with an extremely small market as end of one, and then you just need to achieve product-market fit with 2, and then 4, and then 5."

Takeaway:
  • Start by solving a significant problem for even one customer.
  • Gradually expand your solution to more users.
  • View product-market fit as an iterative process.

How can startups provide value through last-mile integration?

Opening: Focusing on the last-mile integration can help startups offer unique value to enterprises. Quote:

"There's more awareness that voice is a thing... Enterprises, they can't use OpenAI... There's a constant refining and tuning... That expertise is very hard to learn without having done it yourself many times."

Takeaway:
  • Identify gaps where large companies can't serve well.
  • Offer specialized expertise to meet enterprise needs.
  • Build defensibility through unique knowledge and experience.

How did you compete with big players like OpenAI?

Opening: Startups often face competition from large tech companies; focusing on niche value can be key. Quote:

"We thought we were going to be a model company... OpenAI also announced GPT-4 audio... But it kept growing... We saw this happen."

Takeaway:
  • Pivot when market dynamics change due to big players.
  • Find unique value propositions, like last-mile integration.
  • Leverage your agility to serve customer needs better.

How did you handle rapid growth with a small team?

Opening: Managing rapid growth with limited resources poses unique challenges for startups. Quote:

"It constantly felt like that... My co-founder pulled me aside one time and was like, dude, if you don't get me a fucking infrastructure engineer, we are going to die."

Takeaway:
  • Recognize when to scale your team to handle growth.
  • Prioritize critical hires in response to operational strains.
  • Stay responsive to team feedback to avoid burnout.

How did you build conviction to persist through challenges?

Opening: Strong conviction in a big idea can help founders overcome obstacles and uncertainties. Quote:

"I think for the first time as a founder, I just had deep conviction on something very big... because I finally just like believe something that not that many other people seem to believe."

Takeaway:
  • Believing deeply in your vision fuels persistence.
  • Conviction helps navigate through tough times.
  • Unique insights can differentiate your startup.

How important is it to solve a 10 out of 10 problem for customers?

Opening: Identifying and solving a customer's most pressing pain point is crucial for startup success. Quote:

"It's quite important that you just find someone who has a 10 out of 10 burning pain... It's about like pushing on that and getting them to prove to you that it's as painful as it is."

Takeaway:
  • Seek customers with urgent, critical problems.
  • Validate the intensity of their pain through direct questioning.
  • Prioritize solving high-impact issues for better traction.

How did moving to San Francisco affect your startup's direction?

Opening: Changing environments can have a significant impact on a startup's trajectory, especially when founders feel stuck. Quote:

"I think it's more to do with moving... We got stuck in a rut of chasing a local maxima, working on what we worked on before, which is like a calendar app for 3 or 4 years. That moving was like the shock to the system that really did it."

Takeaway:
  • Moving can provide fresh perspectives and break stagnation.
  • New environments can inspire new ideas and opportunities.
  • Embracing change can be crucial for startup success.