Protecting Capital When Startups Don't Scale

What if the best investments aren’t the riskiest—but the ones everyone else can’t own? In this episode, I sit down with Keri Findley, Founder and CEO of Tacora Capital, to discuss how she built one of the most differentiated credit strategies by focusing on illiquidity, not risk. Keri explains how dislocations are often driven by forced sellers and structural constraints, why the best credit opportunities come from creating assets rather than just finding them, and how she partners with startups to finance products banks won’t touch. We also explore portfolio construction, why scaling is the hardest problem in credit, and how incentives, ethics, and alignment ultimately determine outcomes.

Highlights:

• Why illiquidity—not risk—creates the best credit opportunities
• How forced sellers and ratings constraints drive mispricing
• The difference between finding assets and creating them
• Why scaling a credit fund is harder than venture
• How one bad deal can destroy an entire credit portfolio
• Why alignment and ethics matter more than structure
• The hidden equity upside inside credit strategies
• Why solving real problems creates durable alpha

Guest Bio:

Keri Findley is the CEO of Tacora Capital, an investment firm focused on asset-based lending across fintech, insurtech, and specialty finance. She previously built and led the structured credit business at Third Point, one of the world’s leading hedge funds, and has spent her career investing in complex credit opportunities. Keri specializes in structuring and financing assets that fall outside traditional markets, partnering closely with founders to scale new financial products.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank @AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Keri Findley:

LinkedIn:https://www.linkedin.com/in/keri-findley-4a974a10a/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why Being Young Made Her a Better Trader During the Financial Crisis (2:04) The Real Edge Great Credit Investors Have (4:49) The “$100 Bill on the Ground” Trade No One Wanted (7:15) The Mortgage Bond Trade That Changed How She Invests Forever (12:39) Why You Don’t Always Need a Catalyst to Make Money (16:11) How Peter Thiel Became Her Largest LP (21:15) Why Scaling a Credit Fund Can Actually Hurt Returns (30:51) The Deal That Made Her Swear Off Equipment Financing Forever (37:07) Why One Tiny Equity Stake Can Become a Billion-Dollar Outcome (40:44) The Dangerous Trap of Trying to “Speed Run” Your Career