Podcast Summary: "Matt Cohen: Ripple Ventures"

Podcast: The Investor With Joel Palathinkal
Host: Dr. Joel Palathinkal
Guest: Matt Cohen (Managing Partner, Ripple Ventures)
Date: August 17, 2025

Main Theme / Purpose

This episode dives into Matt Cohen’s transition from Wall Street trader to founder, and ultimately to institutional venture investor as leader of Ripple Ventures. The conversation spotlights Matt’s learnings from traditional finance, lessons from building a bootstrapped startup, his operator-first approach to early-stage investing, strategies for working with LPs, and advice for both founders and emerging managers. Listeners gain in-depth insight into the realities of public and private markets, fundraising, and the changing landscape of venture capital.

Key Discussion Points & Insights

1. Wall Street Beginnings and the Transition to Venture (00:00 - 12:24)

• Early Career on Wall Street: Matt recounted his time at RBC Capital Markets, working alongside major players in high-frequency trading (“Flash Boys” era).
  • Hedge fund heyday: “Those were the heydays… arbitrage world on convertible arb and option trading… It was good times. And it all came crashing down even before the crisis when electronic trading started coming to fruition.” (Matt, 04:00)
  • The emergence and crackdown on high-frequency trading, including inside stories from working near Brad Katsuyama, later renowned for founding IEX (the “speed bump” exchange).
• Understanding Market Microstructure: Detailed explanation of how fiber-optic cables and server placement impacted trading speed (06:59), the origins of IEX, and the transition from a tech arms race to self-regulatory market solutions.
• Crypto vs. Traditional Public Markets: Insights on why crypto exchanges are fundamentally different and still lack robust self-regulation. (11:35)

2. Entering the Private Markets: Starting as a Founder (12:24 - 16:30)

• From Epiphany to Entrepreneurship: After seeing the public markets inside out, Matt realized, “There's gotta be something that happens before a company goes public… I wanted to learn about that.” (Matt, 12:24)
• Founding Turnstile Solutions: Bootstrapped a WiFi marketing analytics startup in Toronto, turning it into a multi-million-dollar company ultimately acquired by Yelp (~$30M CAD).
• Bootstrapping through Adversity:
  • “We pitched over 320 investors. They all just said no. And they were probably right… There’s great businesses that are bad venture investments, and there are great venture investments that are terrible businesses.” (Matt, 16:30)

3. Acquisitions & Founder Guidance on Exits (16:30 - 23:27)

• Being ‘Bought, Not Sold’: Organic partnerships (e.g., with Cisco) led to the Yelp exit.
  • Advice: “Never go in with the expectation you're going to sell the company. Always go in with, hey, we want to be a partner… mission alignment is very, very important.” (Matt, 17:35)
• Distribution > Product: Discussion on how marketing and visibility often trump raw technology. Stories of other minimal-team exits (e.g. Plenty of Fish, Grindr).
  • “There was a great Twitter thread… about how because of the PR and marketing the guy did around his early stage venture… he sold the company for 100 million.” (Matt, 20:09)
• Caveats of Bootstrapping: Bootstrap wins are rare and require immense personal sacrifice.

4. Building Ripple Ventures: The Operator-First Fund (24:59 - 29:01)

• Founding the Fund: Used proceeds from Turnstile and early Ethereum exposure to seed Ripple Ventures.
• Thesis: B2B SaaS, operator-first, hands-on incubation.
  • “We ended up launching our own incubator space in downtown Toronto… so we can help them get through that valley of death that most startups fail in.” (Matt, 24:59)
• Metrics and Validation: Early Ripple funds saw strong co-investment from True Ventures, Felicis, Amazon, et al. Fund 1 vintage top 5%.

5. Lessons on Fundraising, Reporting, and Working with LPs (29:01 - 42:31)

• Zero Institutional in Fund 1: Chose to build track record first.
• Transparency and Trust: “We were overcommunicative with our LPs early on, like monthly updates, really, really detailed quarterly updates…” (Matt, 29:01)
• Founder Focused: "Our founders are our clients in the short term and our LPs are our clients in the long term." (Matt, 29:01)
• Fund Strategies: From pre-seed to Series A, concentrated bets, aversion to “spray and pray,” and creative use of SPVs and direct deals.

6. Emerging Manager Advice and Institutional Best Practices (34:55 - 39:39)

• Early Reporting Discipline: “When I was even in angel investing, I would write investment memos for myself… some of the lack of investment memos written… it’s literally just, here's the TechCrunch article… that's it.” (Matt, 34:55)
• Venture Metrics Breakdown:
  • MOIC: Multiple on Invested Capital; best for early value tracking.
  • TVPI: Total Value to Paid-In Capital.
  • DPI: Distributions to Paid-In; “where the money’s made,” essential after the midpoint of a fund’s lifecycle.
• Audit and Admin Best Practices: Starting institutional-grade practices even with small funds pays off later.

7. Fundraising, Storytelling, and LP Pipeline Building (40:14 - 49:01)

• Storytelling Over Selling: “If you ask for money, you get advice. If you ask for advice, you get money.” (Matt, 40:14)
• Keeping LPs Engaged: Regular updates, founder references, showcasing a “human element” via content and podcasts.
• Building LP Relationships: Emphasizes CRM usage, regular communication, and creating “top-of-mind” presence. “Your life’s network is going to be part of your network with your venture fund if you decide to launch one.” (Matt, 47:57)

8. The Ripple Platform: Beyond Venture (42:31 - 46:54)

• Diversification for LPs: Ripple Group offers VC funds, real estate, private equity, and SPV co-investment options.
  • “We have a commercial and industrial real estate fund called Ripple Developments that our LPs enjoy working with as well.” (Matt, 42:31)
• Strategic LPs: Names Tiger Global’s Lee Fixel, David Sacks (Craft), and Roham from Dapper Labs as LPs offering both capital and network.

9. Investment Thesis & Sectors (49:43 - 53:14)

• Focus:
  • Industry agnostic, North American founders.
  • Data-driven platforms (low-code/no-code, workflow automation).
  • Web3 and the creator economy:
    • “Anyone’s a creator… How do you allow someone to diversify their income stream and make it as easy as possible for them to do multiple different tasks while earning an income from it?” (Matt, 51:43, 53:14)
  • Avoids deep tech, life sciences; gives back via student-focused diversity programs.

10. Advice for Emerging Managers, Founders, and Job Seekers (53:47 - END)

• Mentor Wisdom:
  • “Focus on the process, not the end result. It's always important to learn new skills, exercise new muscles, even if the outcome is not really what you hoped it would be.” (Matt, 53:47)
  • “Money will never replace you as the driver. It will just get you there faster.”
• Breaking into VC: Show value first: “When someone goes around the front door and shows their way of adding value before even asking what they want… I love that.” (Matt, 56:09)

Notable Quotes & Memorable Moments

• “There’s great businesses that are bad venture investments, and there are great venture investments that are terrible businesses. That’s like the Uber model.” (16:30)
• “Never go in with the expectation you're going to sell the company. Always go in with, hey, we want to be a partner.” (17:35)
• “If you ask for money, you get advice. If you ask for advice, you get money.” (40:14)
• “Your life’s network is going to be part of your network with your venture fund if you decide to launch one.” (47:57)

Timestamps for Key Segments

• 00:00-04:00: Wall Street / Trading “Flash Boys” Era
• 06:59: The Value of Fiber-Optic Arbitrage in High-Frequency Trading
• 12:24: Matt’s Founding Epiphany; Entering Private Markets
• 16:30: Bootstrapping Turnstile, Lessons on Venture (and Not)
• 21:20-22:32: Bootstrap Exits: Plenty of Fish, Grindr
• 24:59: Starting Ripple Ventures and the Operator-First Model
• 29:01-34:00: LP Relations, Transparency, and Reporting
• 37:38: Key VC Performance Metrics Explained
• 40:14: Storytelling and Fundraising Lessons
• 42:31: The Ripple Group: Offering LPs More than VC
• 49:43: Investment Focus and the Modern “Creator Economy”
• 53:47: Final Mentor Advice and Words for Emerging VCs

Additional Resources

• Ripple Ventures Fellowship: fellowship.rippleventures.com
• Ripple Ventures Podcast ("Tank Talks")
• Matt Cohen on Medium/Twitter for further insights

Tone & Style:
Matt speaks candidly, weaving anecdotes and actionable wisdom with humility and a pragmatic outlook honed by his diverse experience. Joel’s questions are fluid and engaging, making the episode highly educational, especially for emerging investors and operators.

For those who haven’t listened:
This episode is a goldmine for aspiring fund managers, angel investors, operators-turned-investors, and founders curious about capital formation and partnerships in tech. Matt Cohen demystifies both sides of the table with transparency and practical guidance.