What if the way you’ve been thinking about startup fundraising is... totally outdated?
In this episode of Perception Paradox, I sit down with Jeffrey Fidelman, a former Wall Street pro turned startup investment strategist, to break down what’s actually working in fundraising today.
We explore:
How “Fundraise as a Service” is flipping the script for founders
The biggest mistakes startups make when pitching investors
Why personalized outreach matters more than ever
The surprising power of crowdfunding in 2025
How AI is slashing startup costs and changing investor expectations
And one big question every founder should ask: “Does my startup actually improve the industry I’m in?”
Whether you're raising your first round or just trying to understand the capital game — this episode gives you the fundraising clarity you didn't know you needed.
🎧 Tune in and get smarter about your next raise.
About Jeffrey:
Jeffrey Fidelman is the Founder and Managing Partner of Fidelman & Company, an advisory firm he launched in 2015 to help early- to mid-stage companies with fundraising and growth strategy. Under his leadership, the firm has grown to a 40+ person remote team supporting clients across capital raises, business sales, and strategic initiatives.
With deep experience as an interim CFO and COO, Jeffrey has guided dozens of companies through pivotal financial transactions. His career spans residential and commercial real estate, Portfolio Manager at Morgan Stanley, Vice President at HSBC, and Partner at an early-stage venture fund focusing on tech startups.
A Harvard graduate (cum laude), Jeffrey has built a reputation as a strategic operator, investor, and trusted advisor to founders and management teams.
Chapters
00:00 Introduction to Fundraising and Startups
03:37 The Journey from Finance to Investment Banking
06:44 Fundraise as a Service: A New Approach
09:38 Shifts in the Startup Ecosystem
12:19 The Impact of AI on Innovation
15:12 Investor Landscape Changes Post-COVID
18:02 The Importance of Structured Outreach
20:58 Asking for Capital: The Founder’s Responsibility
26:20 The Importance of Asking for Funding
27:41 Common Fundraising Mistakes
29:55 The Fundraising Timeline
33:55The Future of Fundraising and Revenue Expectations
35:46 Crowdfunding as a Viable Option
39:17 Emerging Trends in the Startup Ecosystem
45:27 Philosophical Reflections on Building Businesses
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