[Venture Capital Series] How Venture Capital Really Works Beyond the Myths With Mike Collins

Mike Collins is the Founder and CEO of Alumni Ventures, a leading venture capital firm that enables individual accredited investors to access diversified venture portfolios and co-invest alongside top-tier VCs. He is a serial entrepreneur and experienced venture capitalist who has founded multiple companies, including Kid Galaxy, Big Idea Group, and RDM. He also launched Green D Ventures, Alumni Ventures’ first alumni fund, where he oversaw the portfolio as Managing Partner. Mike has spent his career helping investors and entrepreneurs build innovative, high-growth businesses, and holds degrees from Dartmouth College and Harvard Business School.

Here’s a glimpse of what you’ll learn:

• [4:52] Mike Collins explains how asking “what is right” guides tough business decisions
• [8:28] Business lessons from sports and guarding Michael Jordan
• [11:51] Why VCs embrace failure and focus on finding a few big winners
• [15:43] Mike shares Alumni Ventures’ biggest missed investment opportunities
• [20:55] Why venture capital risk drops with 100+ company portfolios
• [26:53] How co-investment creates unique advantages over lead investing
• [33:23] Tips on joining and customizing Alumni Ventures’ investment funds
• [36:15] The global strategy behind the Japan-US Bridge Fund launch

In this episode…

What does it really take to succeed in venture capital, where uncertainty is constant, and failure is often part of the process? What separates investors who consistently build strong portfolios from those who don’t?

For Mike Collins, a seasoned venture capitalist and serial entrepreneur, success in venture capital comes from focusing on people over pure ideas and building disciplined, diversified portfolios to manage inevitable risk. He highlights that early-stage investing is less about certainty and more about judgment, trust, and pattern recognition developed over time. A key takeaway is that long-term success stems from striking a balance between conviction and humility and accepting that many investments will fail while a few yield outsized returns. He also emphasizes the value of co-investing and leveraging a global investor community to expand access and insight.

In this episode of the Inspired Insider Podcast, host Dr. Jeremy Weisz sits down with Mike Collins, Founder and CEO of Alumni Ventures, to discuss venture capital, portfolio building, and entrepreneurial lessons. They talk about betting on people over ideas, managing risk through diversification, and lessons from sports and investing. Mike also shares insights on co-investing strategies and democratizing access to venture capital.

Resources mentioned in this episode:

• Mike Collins on LinkedIn
• Alumni Ventures
• Green D Ventures’ Fund and Syndicate
• Kid Galaxy
• The Innovator’s Dilemma: The Revolutionary Book That Will Change the Way You Do Business by Clayton M. Christensen
• Zero to One: Notes on Startups, or How to Build the Future by Peter Thiel, Blake Masters
• The Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses by Eric Ries
• Jensen Huang on LinkedIn
• Xanadu
• OpenAI
• Anthropic
• Oura Ring
• Sleeper
• Meet the AV 100
• Andreessen Horowitz
• Sequoia Capital
• Khosla Ventures
• Baby Academy
• Slack
• Zoom
• SpaceX
• ChatGPT
• Claude
• Mike’s 100 Venture Greatest Hits
• Here are the highlights from Mike’s Greatest Hits

Special mention(s):

• Kevin Landry

Related episodes:

• “[Venture Capital Series] Triaging Growth Challenges in Startups With Brett Browman” on Inspired Insider Podcast
• “[Venture Capital Series] Investing in Purpose-Driven Companies With Eva Yazhari” on Inspired Insider Podcast
• “[Venture Capital Series] A Framework for Making Important Decisions with Fabrice Grinda of FJ Labs” on Inspired Insider Podcast

Quotable moments:

• “A lot of business success comes from daily incremental improvement, not just big ideas.”
• “In venture capital, even a 250 batting average is strong because one or two winners drive returns.”
• “In uncertainty, I believe you win by betting on the people behind the idea.”
• “Great entrepreneurs often seem crazy at first because they see the world differently.”
• “Venture capital is for optimists focused on what can go right, not only what can go wrong.”

Action steps:

1. Build a diversified portfolio to manage risk and capture outsized wins: Spreading investments across many companies reduces the impact of failures while increasing exposure to rare, high-return opportunities driven by the power law.
2. Focus on incremental improvement as a daily discipline: Consistent, small gains over time are more reliable than chasing a single breakthrough idea, reinforcing the importance of persistence and steady execution.
3. Bet on people over ideas in early-stage investing: Strong, adaptable founders can navigate uncertainty and pivot when needed, making team quality more important than perfect plans or early metrics.
4. Engage in continuous learning and active networking: Participating in investor communities, events, and educational programs helps sharpen decision-making and improves access to better opportunities.
5. Embrace failure while maintaining long-term optimism: Setbacks are inevitable in venture capital and entrepreneurship, but resilience and a forward-looking mindset help investors learn from them and stay focused on achieving long-term success.

Episode Transcript

Intro 00:15

You are listening to Inspired Insider with your host, Dr. Jeremy Weisz.

Dr. Jeremy Weisz 00:22

Dr. Jeremy Weisz here. I am the Founder of InspiredInsider.com, where I talk with inspirational entrepreneurs and leaders. Today is no different.I have Mike Collins. You can find them at av.vc. It’s Alumni Ventures. Mike, I’m going to formally introduce you. Before I do, I like to point out other episodes of the podcast. People should check this out. This is part of the Top Venture Capital Series. I had Brett Browman, who’s just worked as a growth operating partner at Khosla Ventures. I had Eva Yazhari, who was really investing in purpose-driven companies. Another interesting Fabrice Grinda of FJ Labs, and so many more just interesting takes on there. And Mike, I don’t know, do you have some colleagues, mentors in the space that you want to talk to that you’ve learned from?

Mike Collins: 01:11

Yeah, I mean, I, one of my big early mentors was a guy named Kevin Landry, who was the Founder, really managing partner in the formative years of a venture capital firm called TA Associates in Boston. You know, Kevin was a force of nature. And really, I joined the firm as kind of a know-nothing 21-year-old and really learned a lot just by watching him interact with entrepreneurs. This is a while ago. This is 1986. And then another big influence of mine was Clayton Christensen. A lot of people will have heard of his book The Innovator’s Dilemma and the term kind of disruption, which he kind of coined. Really just a legendary figure in the area of technology and innovation. And, you know, huge inspiration for me and a real privilege to get to know Clay. So those two guys in particular just had a really early, impactful influence on my life and career.

Dr. Jeremy Weisz: 02:26

Clayton is definitely in my Audible library. Kevin, there’s a point where you tried to leave, and Kevin tried to stop. You talk about that for a second, and what did what did. How’d that conversation go?

Mike Collins: 02:43

I mean.

Mike Collins: 02:43

This was.

Mike Collins: 02:44

You know, I was on the path of. Going back to business school. So I had actually gone to Dartmouth as an undergraduate and joined the associates in 1986. And, you know, I loved it and I, I was pretty good at it, I think. And, you know, I had just, you know, was getting ready to go back to business school and frankly, heading back up to Hanover to go to Tuck. And, you know, Kevin came in and said, why would anybody ever want to go to business school? You know, I go, you went to business school, you went to Wharton. What are you talking about? And he goes, blah, blah, blah, blah. And he goes, okay, well, what do you need to do to stay at least a couple more years? And I said, well, I hadn’t thought about it, but, you know, you gotta, you gotta promote me to the level of, you know, the work I think I’m doing and I’m going to take a couple months off and go, you know, hitchhike around Australia and New Zealand and just how much money you’re going to pay me It was done. He walked out the door, walked out of the office. Kevin had no problem in making kind of quick decisions, and I kind of like, whoa, okay, I guess I should ask for more, but.

Dr. Jeremy Weisz: 04:07

Right.

Mike Collins: 04:08

But yeah. And then it kind of one thing led to another. And I, I met the woman who eventually became my wife, and I ended up actually going, staying in town, you know, and kind of good, good will hunting follow the girl and stayed in Boston and went to HBS. And that’s where I met Clay. So, you know, it’s like Steve Jobs says in his commencement speech that most people have heard about and listened to, which is, you know, that that’s only makes sense looking backwards. And, you know, those were, you know, those were a couple of the dots that got connected for me.

Dr. Jeremy Weisz: 04:47

Obviously, Kevin was a mentor. What were some of the things you learned from him?

Mike Collins: 04:52

I think he was. I remember a couple of things. His. What is the right thing to do was really, you know, pros, cons, boom, boom, boom. But there are always times in life and in business where it’s just like, you know, you can lose sight of that. And so I think part of the DNA of like, what is the right thing to do in this situation, just was imprinted on me because he would always say that. I think he was also a great example of being really kind, tough-minded, and soft-hearted. And so he would, he would, he would take an issue or a problem or a, you know, an issue that he felt existed with one of our portfolio companies. And he would be as rigorous and tough on that problem as one could possibly be. But he was very empathetic and fair and understood the human side of life and business. So, you know, I think those two things were things that really. You know, I think you get disproportionately imprinted on some of those early mentors and bosses and work experiences. And, and, and those were a couple for me.

[Continue to Page 2]