Meet Mike Lazerow, the serial entrepreneur and investor with a knack for being ahead of the curve.
You might know him as the co-founder of Golf.com, which he sold to Time Warner in 2006, or as the mind behind Buddy Media, the leading social media marketing platform acquired by Salesforce in 2012 for a cool $745 million.
While his track record of multi-million-dollar exits is impressive, Mike hasn’t slowed down. He has since become a powerhouse angel investor and advisor, supporting nearly 100 early-stage startups, including major players like Scopely and Liquid Death.
Now, Mike is leaning into a new mission. Without taking his foot off the gas, he’s focused on helping the next generation of business master the complex realities of building and scaling businesses, all while prioritizing a deeply present and meaningful life.
We sat down with the seasoned builder to talk about his near-death experiences, the surprising way he channels fear, and his secrets to a good life.
What inspires you the most, in and out of work?
At work, I’m inspired by people who show up when it’s not glamorous—the builders who keep digging even when the mud’s up to their knees. The founders who take the punches and still believe,putting in the work every day. Outside of work, it’s simple – my family. Kass has been my inspiration for close to 30 years now. And our kids are adults charting their own course and building lives of their own, which is inspiring to see. They remind me what actually matters: love, laughter, and presence.
You’ve had two near-death experiences. What have they taught you about how to live Did it change your perspective on risk and time?
Almost dying twice gifted me the clarity to live. Before seeing my death, I was riddled with fear and stress. After I stopped worrying about what others thought. I stopped being scared to act – to jump, to ask a girl out, to take risks. Those near-death moments taught me to move — not recklessly, but honestly. To stop hedging joy like it’s a limited commodity. I felt like I was now playing in overtime. I was given more time, time that I wasn’t supposed to have, to live, to win. Now I ask myself two questions: What’s the worst that can happen if I do this? Usually, not much once you remove fear from the equation. And what’s the best that can happen if I succeed? The upside almost always wins.
What are you doing when you aren’t working?
My interests haven’t changed much since college. I still love live music — Phish is my forever band — but I’m no purist; I’ll listen to anything that moves me. I golf and fly-fish when I can, and I’m proudly the fourth-best pickleball player in my own family. I’ve also got a thing for sneakers. I collect them, but I wear every pair. Most of my time goes to my family and the same crew of friends I’ve had since high school and college. They keep me laughing, humble, and honest. And yes, I’m still a Northwestern fan, which means I’ve mastered the art of loyalty and Disappointment.
Some people might make a sale like Buddy Media and retire altogether. What keeps you in the game?
I tried to retire once. After four years at Salesforce, I thought I’d trade business plans for paintbrushes. I love painting — still do — but focusing on it full-time taught me a hard truth: passion doesn’t always equal talent. When you love something but aren’t great at it, that’s a hobby, not a calling. I wasn’t fulfilled; I was drifting. So I came back to building. Entrepreneurs don’t really retire, we just change what we’re building. For me, creation is oxygen. I live for that space between “this might work” and “we’re completely screwed.” That tension means I’m alive. I’m not chasing trophies anymore — I just like the mud.
How do you spot the next best ideas?
I have a beginner’s mind. I consume a ton of information everyday. When something interests me, I go down the rabbit hole and oftentimes come out with ideas. All of my companies so far have been at the forefront of a new technology or cultural shift, from the rise of the commercial internet to social media and mobile technologies to blockchain, and most recently, AI.
The best way I have found to stay on top of the most important trends is to talk to smart builders, or follow them on social media. The builders I respect the most are focused on problems that matter. And if enough of them are working on something, usually it’s something worth paying attention to. The best ideas look a little stupid at first. If everyone gets it right away, it’s already too late.
What do you want to learn more about in the next year?
I’m obsessed with the intersection of AI and small business. Businesses without significant resources will benefit the most from the greatest productivity tool of all time. Personally, I’m on a wellness mission and my latest area of exploration is stillness. I’ve spent my life in motion—startups, deals, deadlines, workouts, kids, commitments, more, more, more. Being still is new territory. I’m learning how to sit quietly, to put the phone down, to be where my feet are. It’s surprisingly uncomfortable, which probably means I need it.
What’s the single most important question you ask a founder before writing a check?
What is your vision for the company and what are the top 3 things, in stack-ranked order, you need to do to close the gap between your vision and your reality? I’m not looking just for the content of the answer. I’m trying to understand how focused the founder is. Does she know where she wants to go? And if so, does she have a plan that will get her in a reasonable timeframe? You would be surprised how many founders don’t know what they want to accomplish if they succeed. And how many have a clear goal for the business but no clue what they need to do to reach it. A focused founder who loves to shovel is unstoppable. An unfocused founder, regardless of work ethic, will never succeed.
If you could give 20-year-old Mike one piece of advice, what would it be?
I was always in a rush. When I was 3 I wanted to be 6 like my older brother. When I was in college, I wanted to work for my own company. I always felt behind. I now tell young people I meet with what I wish I had known at the time. You’re not behind. No one has it figured out. Keep doing the right things every day, week, month and year and good things will happen. Time is on your side. Also, maybe buy some Nvidia and Apple stock when you can!
How do you apply the principle of “conquering fear” to your everyday life? (Work and personally)
Fear is energy. It is everywhere and nowhere at once. It’s omnipresent. And it can’t be created or destroyed. It can only be transformed from one form to another. Once I realized that fear doesn’t go away, I started to channel it. Fear went from paralyzing me to powering me. It’s the voice of doubt and uncertainty that says this idea’s stupid, you’ll fail, people will laugh… It’s the counter to my entrepreneurial voice that tells me I can do anything. So, I don’t “conquer” fear just like I don’t “conquer” my entrepreneurial drive. I work with both and listen to them both like a trusted partner, not an enemy. When something scares me, it usually means it matters. So I move toward it deliberately. Great businesses come from pain – also known as problems that exist in the world asking to be solved. So lean into the pain. In life, living fearlessly means saying what I actually feel before it’s too late. Speaking my truth. Fear used to run the show. Now it’s just a co-pilot — nervous, loud, but along just for the ride like all the other emotions that make me human and unique.
What is your secret to living a good life?
Spend 80 percent of your time building relationships and pursuing your purpose. Both will make mornings lighter and nights peaceful. Use the rest to do what you love. And through it all, remember to laugh.
