129: From a $5M Cold Call to a $1B Comeback: Cole Wilcox of Longboard Asset Management on the Fundraising Grind and Founder Resilience

Everyone loves a success story, but what we don’t talk about enough is what it costs to get there.

And what it’s like before the money is wired or anyone cares.

Before all of that, there was a guy with a phone, a thesis, and a long list of people telling him no.

That guy was Cole Wilcox.

In this episode, Stacy Havener sits down with Cole, CEO & CIO of Longboard Asset Management, to talk about what it really takes to build an investment firm when you don’t start with pedigree, proximity, or institutional backing, just conviction and the willingness to keep going when quitting feels rational.

In this episode, you’ll hear:

• How one cold call turned into Longboard’s first $5M

• Why founder-led fundraising is unavoidable in the early years, no matter how strong your strategy is

• What it feels like to hear “call me at $100M”… and then hear it again at $1B

• How surviving multiple market crises permanently reshaped Cole’s relationship with risk

• The moment Longboard nearly shut down, and the structural pivot that kept the firm alive

• The real cost of broken partnerships (and why people issues end more firms than markets)

• What resilience actually looks like when walking away feels like the logical move

• Why staying power might be the most underrated edge a founder has

More About Cole:

Cole Wilcox, Chief Investment Officer at Longboard, has specialized in trend following investment strategies for over 20 years. As a co-author of award-winning research, he has been profiled in bestselling investment books, featured in major media outlets such as The Wall Street Journal, CNBC, and Bloomberg, and is a frequent guest on popular podcasts. Cole leads a highly accomplished team at Longboard, delivering innovative, low-correlation investment strategies that leverage trend following to capture market opportunities.

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