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Startup Fundraising: Raise, Bootstrap, or Both? Lessons from Founders and Investors

Should you raise venture capital or grow on your own revenue? Few startup questions get more airtime on podcasts, and the answer depends a lot on who's talking. This page collects 14 moments where founders and investors take it on directly, from Y Combinator, The Twenty Minute VC, The Indie Hackers Podcast, a16z, Below the Line and other shows. Justin Kan explains when raising a lot made sense for his company. Sahil Lavingia explains why Gumroad's steady growth couldn't land a Series B. Mark Cuban and Dave McClure share the math they use when they invest. Each note is a question, a short answer, and the minute it was said, with a link to the full episode. The notes are grouped into three parts: deciding whether to raise at all, understanding how investors think, and what early rounds look like in practice. Use it as a starting point, and listen to the full conversations before you decide anything for your own company.

Should you raise at all?

  1. Should You Raise A Lot Of Money Or Bootstrap To Profitability

    Justin Kan warns that big rounds lead to big spending, then explains why raising heavily still made sense for Atrium.

    a16z · Startup Lessons from Serial Entrepreneur Justin Kan · at 13:56

  2. What Makes Self-funded Startups So Attractive To A Vc-backed Founder

    Ryan Hoover's one-word answer is control over your cash flow, ambitions and expectations.

    Below the Line with James Beshara · Ryan Hoover — Products of our Environment · at 16:22

  3. What Do You Do If Investors Don't Want To Invest

    Flexport's Ryan Petersen lays out the options: change the business, fund it yourself, or fund it with customer revenue.

    Y Combinator · Ryan Petersen of Flexport on Compounding Success and Winning · at 53:16

  4. Why Did Gumroad Struggle To Raise Series B

    Sahil Lavingia on why a solid but slower-growing company doesn't fit what venture investors need.

    The Indie Hackers Podcast · #100 – From Aspiring Billionaire to Indie Hacker with Sahil Lavingia of Gumroad · at 55:07

How investors think

  1. What Are Vcs Looking For In Real-product Businesses

    Dave Schappell's short list is cash flow, big margins and high repeat order rates.

    Kruze Consulting's Founders and Friends Podcast for Startups · Dave Schappell on raising venture capital as a repeat entrepreneur · at 23:57

  2. How Does Mark Cuban Think About Startup Investing

    Mark Cuban looks for companies whose cash flow alone could pay back his investment.

    The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch · Mark Cuban on His Relationship To Wealth and Risk and Why Silicon Valley Investors Are Like Old Hollywood · at 13:09

  3. Does A Fund Need To Invest In A Unicorn Startup To See Good Returns

    Dave McClure walks through 500 Startups' portfolio math and when a fund actually needs a unicorn.

    The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch · 20VC: 500 Startups' Dave McClure on Whether Unicorns Are Necessary For Venture Returns & Why Ownership Is Not The Math To Think About When Investing · at 6:26

  4. Does The World Have Enough Vcs And Vc Money

    McClure on how venture money clusters in a few hubs while much of the world has far less.

    The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch · 20VC: 500 Startups' Dave McClure on Whether Unicorns Are Necessary For Venture Returns & Why Ownership Is Not The Math To Think About When Investing · at 21:16

  5. What Are Mike’s Favorite Things About Being A Seed Investor

    Mike Maples on why seed investing feels more like being a co-conspirator than an investor.

    Below the Line with James Beshara · #2 — Mike Maples · at 4:02

How early rounds come together

  1. Any Tips For Fundraising

    Vinovest's Anthony Zhang recommends getting references through portfolio founders and treating cold email as a last resort.

    Forward Thinking Founders · Anthony Zhang on Wine as an Asset Class · at 24:43

  2. How Do You Get The Most Out Of Investors

    Zhang's advice is to ask for help when you need it and be upfront about problems.

    Forward Thinking Founders · Anthony Zhang on Wine as an Asset Class · at 21:49

  3. When Did Experiment Raise $1.3m In Funding And Who Invested

    Cindy Wu on going from a research lab to a $1.3 million round within a year by showing real-world proof.

    Think Like A Founder · Cindy Wu. Co-Founder of Jelly. · at 5:37

  4. How Much Money Did Scribd Raise After Y Combinator

    A reminder that early YC companies like Scribd sometimes left Demo Day living on savings and help from family.

    Y Combinator · The Challenges Of A Repeat Founder · at 6:55

  5. What Have Been The Biggest Challenges While Raising Capital For Kai Xr

    Kai Frazier on the headwinds she faced raising money for an edtech VR startup, even after Techstars.

    Forward Thinking Founders · FI - Kai Frazier (Kai XR) And VR For Kids · at 12:41