Podcast Summary: Making It with Jon Davids

Episode 206: "We sold for $800M. Here's what happened next."
Guest: Mike Lazerow, Tech Entrepreneur & Investor
Date: August 19, 2025

Episode Overview

In this episode, Jon Davids interviews Mike Lazerow, a renowned tech entrepreneur and investor best known for founding Buddy Media, which sold to Salesforce for $800 million. Lazerow discusses his journey from bootstrapping companies to multi-million dollar exits, his investment philosophies, most significant successes and failures, personal dynamics as a founder, and why focus, relationships, and execution matter most. The conversation blends tactical business advice with personal insight, making it a must-listen for any aspiring or experienced entrepreneur.

Key Discussion Points & Insights

Building and Selling Buddy Media

• Origin and Vision (00:34-01:36)

  • Buddy Media provided software that allowed brands to manage social media presences, founded in 2007. The idea was met with skepticism ("Everyone told us it was a dumb idea because at the time, no one had heard of even Facebook." – Mike, 01:39), but faith in the platform's growth and the strength of his team persisted.
  • Pivotal Decision: Pivoted four times before landing on the successful business model.

• Landing Unilever as a Client (02:04-02:43)

  • Their first major client, Unilever, needed to program content across 100 countries and over 100 brands. Buddy Media won their business by pairing software with "very, very high touch service."

• Team Building (02:43-03:08)

  • Mike credits hiring Jeff Ragavan as transformational: "Relationships are gold. Sales is what keeps people eating and companies alive." (Mike, 02:54)
  • Jeff was onboarded as a co-founder for his sales acumen and relationship-building skills.

• Success Timeline (03:08-03:27)

  • The pivot to software led to tremendous reaction: "0 to 50 million in ARR in three years. Record time for any company at the time." (Mike, 03:12)

Lessons as a Serial Entrepreneur

• Multiple Ventures (03:27-03:43)

  • Mike and his wife Cass have started eight companies together. "It never gets easier... What gets easier is you make fewer mistakes." (Mike, 03:34)

• Funding Experiences (03:43-04:07)

  • Raised money for all companies, sometimes from family (his grandfather gave $5,000 to start U Wire), other times from venture capital ($2M–$100M rounds).

• On Investors (04:07-04:27)

  • "Investors are the ones who provide the money... In an ideal world, you get money from people who aren't investors. I’ve yet to figure out how to find money from people who aren’t investors." (Mike, 04:07)

Investing Successes and Insights

• Most Impressive Leader (04:27-04:50)

  • Mike admires Mike Cesario, CEO of Liquid Death, for his marketing prowess and self-awareness: "Great leaders don’t do what they don’t know how to do." (Mike, 04:30)

• Best Investments (05:10-05:57)

  • Pre-IPO investment in Facebook.
  • Seeding Scopely, sold for $5 billion.
  • On selling Facebook shares: "I'm a seller. You can’t hold on to things forever... It's a little painful, but also sweet because we made money." (Mike, 05:40)

Low Points and Hard Lessons

• Business Lows (05:57-06:26)

  • The failed merger of Golf.com resulted in buying the company back and later selling to Time Warner. "That was very painful. But it had a happy ending with a $25 million sale..." (Mike, 06:03)

• Costly Mistakes (07:41-08:00)

  • Partnering with an incompatible co-founder cost $12 million: "It was a friend who we didn’t have the hard conversations [with]... That ended up losing about $12 million of capital." (Mike, 07:41)

Principles and Philosophy

• Focus is Everything (08:02-08:27)

  • "The number one reason companies fail isn’t just because of money... It’s because of focus... Most companies have shiny object syndrome." (Mike, 08:02)

• Luck and Partnership (08:27-09:34)

  • His wife Cass is the key to his success: "Without Cass, I would probably be homeless or at least maybe in jail..." (Mike, 08:29)
  • They complement each other: "I do sales, I do product... She is the one who really minds the farm and makes sure the crops grow..." (Mike, 09:15)

• Money and Identity (09:34-10:22)

  • "The biggest shock to us wasn’t how we acted, but it's how other people react to you... But money just accelerates and amplifies whatever those traits are that you have." (Mike, 09:56)

Wealth, Investing, and Building Back

• Windfall Moments (10:22-10:50)

  • On selling Buddy Media: "We for half an hour we were super excited and then...what’s for dinner? Who's taking the kids to the doctor? Our life went on." (Mike, 10:25)

• Best Investment Outside Tech (11:25-12:02)

  • Real estate: "We've had both appreciation over the years...and you get income. The more boring, the better for us on that side." (Mike, 11:27)

• Asset Allocation (12:02-13:11)

  • High-risk illiquid deals balanced by income-producing assets ("super exciting" vs. "super boring"). "When you’re young, let time help you out. Don’t get in the way. Let time grow your money." (Mike, 13:08)

• Starting Over (13:11-13:55)

  • If he lost everything: "I would launch a business that I could use my network to sell...If you work hard, you work right, you can grow your money and that’s the only way to do it." (Mike, 13:14)

Notable Quotes & Memorable Moments

• On Sales & Relationships:
  "Relationships are gold. Sales is what keeps people eating and companies alive." (Mike, 02:54)

• On Focus:
  "Most companies have shiny object syndrome. They reach for the shiny object and end up out of business." (Mike, 08:02)

• On Founding Partnership:
  "Without Cass, I would probably be homeless or at least maybe in jail. I don't know what I’d be doing, but she's really...It's all about operations." (Mike, 08:29)

• On Wealth Shock:
  "They assume you’re brilliant. You’re really just the same schmuck you were before you made the money." (Mike, 09:56)

• On Early Wins and Moving On:
  "When you make a ton of money, you’re happy for maybe an hour, two hours, but then you realize that your life is your life and you move on." (Mike, 10:25)

• On Asset Allocation:
  "We like super exciting...and super boring. The more boring, the better for us on that side." (Mike, 12:08)

Timestamps for Important Segments

• 00:34 – Buddy Media’s $800M exit, company origins
• 01:30 – Early skepticism on social media business
• 02:05 – Landing Unilever as first major client
• 02:46 – Importance of hiring Jeff Ragavan
• 03:12 – Explosive ARR growth at Buddy Media
• 04:30 – Admiration for Liquid Death’s Mike Cesario
• 05:10 – Facebook and Scopely investment stories
• 05:57 – Lowest business point: Golf.com struggles
• 06:54 – First side hustle: shoveling driveways
• 07:14 – Most impactful book: "Man’s Search for Meaning"
• 07:41 – Expensive mistake: wrong co-founder
• 08:02 – Why most companies fail: focus
• 08:29 – On Cass, spouse and co-founder
• 09:56 – Biggest shock after becoming ultra-wealthy
• 10:25 – The fleeting thrill of $800M windfall
• 11:27 – Best everyday investment: real estate
• 12:08 – Portfolio strategy: high risk vs. steady income
• 13:14 – How he’d rebuild if starting from zero

Tone & Style

Mike's responses are candid, grounded, and peppered with dry wit and humility, balancing practical advice with personal anecdotes. Jon keeps the interview quick-paced and focused, giving listeners direct, actionable insights.

In Closing

This episode offers an honest, detailed look at the realities of high-stakes entrepreneurship, the importance of the right people, execution, resilience, and a balanced approach to both business and life. Whether you’re starting out or scaling up, Mike Lazerow’s experience is a roadmap for the modern entrepreneur.