Episode 393: From Failed Investments to 70+ Startups with Andrew Ackerman
From losing his entire $25,000 life savings on his first investment to backing over 70 startups, Andrew Ackerman shares proven strategies for evaluating founders, testing assumptions cheaply, and why the best entrepreneurs see deals where others see nothing.
In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Andrew Ackerman, a serial entrepreneur turned early-stage investor and innovation expert. Andrew is currently a strategic advisor and head of Reach Labs at Second Century Ventures, consults on corporate innovation strategies and venture studios, and serves as an adjunct professor of entrepreneurship. He previously served as managing director at DreamIt Adventures, one of the top five accelerator programs in the world. He has invested in over 70 startups and written over 60 published articles for Forbes, Fortune, and other major publications.
WHAT YOU'LL LEARN:
In this episode, you'll discover why Andrew looks for the instinct to hustle for deals rather than focusing on the idea itself, how accelerators fill the gap between friends and family money and proper VC rounds, and why testing assumptions with a five-dollar pack of index cards can save months of development time. Andrew explains the real difference between SAFE notes and convertible notes, what makes lawyers often terrible startup advisors, and the SeatGeek origin story that proves early testing can turn a failing startup into a billion-dollar company.
ANDREW'S JOURNEY:
Andrew's path started with both grandfathers as entrepreneurs, one running candy shops and the other creating insurance products. Coming out of University of Chicago in the 90s when startups weren't a thing, he chose consulting before realizing the startup world had caught up. His first venture Bunk One provided internet services for summer camps and exited successfully. His second startup taught harder lessons through founder drama and failure. Angel investing came accidentally through a pharma deal he admits he had no business making, but getting lucky early hooked him. Eventually he joined DreamIt Adventures, running their New York office.
KEY INSIGHTS:
When evaluating founders, Andrew looks for the instinct to hustle. He shared an example of a founder who rented pencils in fifth grade for a nickel a day. Not sold. Rented. That entrepreneurial DNA shows up early and separates successful founders from everyone else.
The SeatGeek story proves early testing works. A startup in his accelerator tested conversion rates early instead of waiting, discovered they were completely off, pivoted in seven weeks, and built a billion-dollar company.
Lawyers often make terrible startup advisors because their incentive structure is backwards. Billing by the hour doesn't reward speed, and careers focused on avoiding mistakes rather than making deals happen.
Perfect for founders thinking about raising capital, anyone curious about how accelerators work, aspiring angel investors wondering how to evaluate founders, and entrepreneurs who want practical frameworks for testing assumptions.
FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/andrewackerman
FOR MORE ON ANDREW ACKERMAN:
https://www.andrewbackerman.com
https://www.amazon.com/Entrepreneurs-Odyssey-Approach-Startup-Success/dp/1032883545/ref=tmm_pap_swatch_0
http://www.linkedin.com/in/andrewbackerman
https://x.com/andrewackerman
https://www.instagram.com/andrewbackerman/
FOR MORE ON COREY KUPFER
https://www.linkedin.com/in/coreykupfer/
https://www.coreykupfer.com/
Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.
Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!
Guest Bio
Andrew Ackerman is a serial entrepreneur turned early-stage investor who has invested in over 70 startups. He heads Reach Labs at Second Century Ventures, previously ran DreamIt Adventures' New York office, and teaches entrepreneurship. He has written over 60 articles for Forbes and Fortune and authored The Entrepreneur's Odyssey, written as a novel because stories stick better than frameworks.
Related Episodes
Episode 370 - Gerry Hays: Democratizing Venture Capital Through VentureStaking
Episode 350 - Tom Dillon: Understanding Business Valuation and Exit Planning Realities
Episode 89 - Sherisse Hawkins: Capital Raising Journey and Funding Realities
Keywords/Tags
angel investing, accelerator programs, startup evaluation, founder assessment, SAFE notes, convertible notes, early stage investing, venture capital, startup testing, lean startup, DreamIt Adventures, Second Century Ventures, startup validation, startup pivots, SeatGeek
