Relationship vs. Transactional Banking

What if the real edge in venture isn’t price—but who you choose to partner with for a decade? In this episode, I sit down with Jamie Montgomery, Co-Founder and Managing Partner of March Capital, to discuss how long-term relationships, not transactions, drive venture outcomes. Jamie explains why asymmetric upside matters more than negotiating the last percentage point, how conviction and discipline shape follow-on decisions, and why understanding your own biases is critical when doubling down. We also explore capital cycles, liquidity dynamics, and how AI is forcing every company to either reinvent itself or fall behind.

Highlights:

• Why relationships outperform transactions in venture over time
• The “turkey sandwich test” for choosing founders
• How to actually decide when to double down on a company
• Why most investors misunderstand capital cycles and liquidity
• The hidden biases that distort follow-on investment decisions
• How AI is forcing a full reset across portfolio companies
• Why venture returns come from asymmetric outcomes, not pricing
• The real competition for capital most VCs ignore

Guest Bio:

Jamie Montgomery is the Co-Founder and Managing Partner of March Capital, a leading technology investment firm focused on growth-stage companies. He previously founded Montgomery & Co., where he advised and financed hundreds of companies and took dozens public, building deep experience across capital markets and entrepreneurship. At March Capital, he has led investments in category-defining companies such as CrowdStrike and ThoughtSpot, and continues to focus on backing disruptive technologies with long-term compounding potential.

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 Jamie Montgomery:

LinkedIn:https://www.linkedin.com/in/jamiemontgomery/

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) What Weekly Meetings With Charlie Munger Actually Taught Him (1:24) The One Investing Rule Most People Quietly Break (3:20) Why Transactional Thinking Never Builds Real Wealth (5:53) The “Turkey Sandwich Test” That Filters Great Founders (9:09) The Dangerous Bias Behind Doubling Down on Investments (11:15) How a Small Conference Became a Global Power Network (16:07) Why One Great Asset Eliminates the Need for Fundraising (17:05) The $200B Opportunity Most Investors Are Ignoring (20:55) Why Doubling the Economy Still Doesn’t Fix Inequality (27:03) The Surprising Way AI Is Saving Venture Capital (31:29) Why Venture Liquidity Might Be About to Disappear