Founder Files

#25 - How Startups Succeed and Break Through the $1M to $10M Stage (Andrew Ackerman)


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Meet Andrew Ackerman, 2x founder, VC investor with 70+ early-stage investments, accelerator operator, and author of The Entrepreneur’s Odyssey.


We sit down with Andrew to unpack what actually drives startup success, from early traction to scaling past the first million in revenue. Drawing on decades of operating, investing, and mentoring founders, Andrew shares a clear-eyed view of what works, what fails, and why.


Topics covered:

  • How investors define growth and traction at each stage

  • Why most startups fail and what failure really means

  • Business vs. venture-scale startup thinking

  • Why founders get stuck around $1M in revenue

  • What scalable go-to-market really looks like

  • Fundraising in tough markets and how to approach it

  • When financials need to be cleaned up and why it matters

  • Early hires and fractional roles founders should not delay

We also dive into Andrew’s book, The Entrepreneur’s Odyssey: A Novel Approach to Startup Success, a story-driven guide that pulls together real startup lessons into one practical, readable framework for founders.


More about Andrew:

  • Buy The Entrepreneur’s Odyssey on Amazon

  • Visit Andrew’s personal site

  • Connect with Andrew on LinkedIn

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Founder FilesBy Cypher