Welcome to Founder Real Talk, a podcast for founders, by founders.
We explore the real journey of building and growing a company. Each episode, we go beyond the highlight reel to unpack the strategies, decisions, and hard lessons that shaped successful businesses, revealing the good, the bad, and the ugly behind the growth.
This week, Josh sits down with Jeffrey Fidelman, a multi-time founder and CEO of Fiddleman & Co. — a firm that helps startups and emerging funds raise capital through investor outreach — and soon-to-launch Fundex, a CRM built specifically for the fundraising process. Jeff spent his early career at Morgan Stanley, HSBC, and as a VC partner before realizing early-stage fundraising was fundamentally broken by misaligned incentives. Eleven years into running his own business, he opens up about why "failing correctly" is harder than winning, the scientific method he applies to fundraising campaigns, and the line from another founder that hit him harder than he expected.
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Chapters
(00:00) - Intro
(02:05) - Why early-stage fundraising is fundamentally broken
(05:37) - The paradox: founders need help raising, but paying for help looks bad
(11:16) - Why this problem became Jeff's passion
(14:38) - A win this year: more capital raised than all of last year combined
(16:38) - Failing correctly is hard. Winning is easy.
(21:03) - The scientific method for testing a fundraising campaign
(23:15) - Setting the right expectations (and refusing to sell snake oil)
(29:59) - Evolving as a leader: being the conduit for your team and your clients
(33:42) - Investing in yourself: outlets, outsiders, and the gym
(36:57) - The 10-year overnight success
(37:10) - Closing thoughts
Links & Resources
- Jeff’s LinkedIn: https://www.linkedin.com/in/jeffreyfidelman
- Fidelman&Co: https://fidelmanco.com/
Keywords
founders, entrepreneurship, fundraising, venture capital, investor relations, capital raising, Fiddleman & Co, Jeffrey Fidelman, Fundex, CRM, seed stage, Series A, pre-seed, misaligned incentives, founder-led fundraising, scientific method, A/B testing, company culture, remote teams, delegation, leadership investment, overnight success, founder resilience