What Happens When a Startup Runs Out of Money | The Financial
Operator Podcast | Episode 76
What happens when you do everything right, and still run out of money?
In this episode of The Financial Operator: Cash In, Chaos Out, Jen sits down with
Andrew Ackerman, Head of REACH Labs at Second Century Ventures, to unpack the
realities of startups, fundraising, and what actually separates the companies that survive
from the ones that quietly disappear.
Andrew shares his firsthand story of building a startup that was gaining traction until a
single world-changing event erased a signed term sheet overnight. From there, the
conversation expands into what founders really need to understand about capital,
leverage, timing, and decision-making.
This episode covers:
• What to do when funding disappears at the worst possible moment
• Why "just take the money" is often the smartest early decision
• The difference between venture-backed startups and traditional businesses
• When fundraising should (and should not) be your full-time job
• Why testing ideas cheaply beats building the wrong thing perfectly
• The traits Andrew sees consistently in founders who succeed
• How to find the one clear message that makes customers stop and listen
If you're building a startup, considering raising capital, or trying to decide whether growth
should be funded or earned, this conversation will give you clarity without hype.
Watch now for a grounded, real-world look at startups, money, and making better
decisions earlier.
⏱️ Timestamps
00:00 Introduction & Guest Welcome
00:26 The Moment Andrew's Startup Ran Out of Money
02:10 Why Early Funding Can Disappear Overnight
03:20 "Just Take the Money": Lessons on Leverage
04:18 Which Businesses Should (and Shouldn't) Raise Venture Capital
06:57 Equity, SAFEs, and Convertible Notes Explained
08:37 When Founders Should Start Fundraising
11:47 Andrew's Path From Founder to Investor
16:14 Inside Accelerators and Early-Stage Investing
20:16 The Traits Andrew Sees in Successful Founders
25:32 Why Stories Teach Better Than How-To Guides
28:52 Testing Ideas Before Spending Real Money
33:39 Renting vs. Buying in the Early Stages
36:18 Finding the One Message That Stops Customers
45:03 Final Advice for Founders
49:00 Andrew's Book & Where to Find Him
To connect with Andrew Ackerman's website: https://www.andrewbackerman.com
Buy "The Entrepeneur's Odyssey" here: https://www.amazon.com/Entrepreneurs-Odyssey-Approach-Startup-Success/dp/1032883545/ref=tmm_pap_swatch_0
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