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ASOM

EP 23: Funding vs. Bootstrapping: An Entrepreneur's Biggest Decision

EP 23: Funding vs. Bootstrapping: An Entrepreneur's Biggest Decision

by John Roman

4 weeks ago


EP 23: Funding vs. Bootstrapping: An Entrepreneur's Biggest Decision

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In this episode of the ASOM Pod, hosts Jimmy Kim (CEO of eCom Email Marketer & Founder of Sendlane), John Roman (CEO & Co-Founder of BattlBox), Amer Grozdanic (CEO & Co-Founder of Praella), and Bryan MacDonald (Director of eCommerce at Oma's Pride) dive into one of the most pivotal decisions for entrepreneurs: choosing between external funding and bootstrapping. They bring together insights from their own entrepreneurial journeys and perspectives from other founders, exploring how each approach shapes a business’s growth, control, and risk profile.

What You’ll Learn:

  • The pros and cons of fundraising versus bootstrapping for new ventures
  • How growth speed and business control differ between funded and self-funded businesses
  • Key market trends, including crowdfunding and venture capital shifts
  • How economic cycles influence funding opportunities
  • Personal stories of fundraising wins, bootstrapping challenges, and lessons learned
  • Tips for assessing whether to raise capital or stick to bootstrapping based on your goals

Whether you’re weighing funding options or simply interested in understanding how these choices impact long-term success, this episode offers a balanced guide to help entrepreneurs navigate growth, risks, and the evolving investment landscape.

00:00 Teaser Trailer
00:09 Personal Experiences with Bootstrapping
00:43 Pizza Talk and Casual Banter
01:30 Starting the Podcast: Meet the Hosts
02:44 Fundraising vs. Bootstrapping: Key Considerations
10:22 Deep Dive: Timing and Growth in Fundraising
14:38 Investor Perspectives and Risk Tolerance
19:03 Mindset and Growth Strategies
26:01 Investor Relationships vs. Entrepreneurial Freedom
29:18 John's Acquisition Journey
30:17 The Freedom of Entrepreneurship
32:38 Bootstrapping Challenges and Strategies
36:18 Fundraising Failures and Lessons
42:19 The Future of Investment and SaaS
48:54 Buy or Sell: Business Insights
52:21 Closing Remarks and Future Topics