About
Serial founder, early-stage investor, speaker, and NYT…
Articles by Michael
Activity
130K followers
-
Michael Lazerow posted this$515 million. That is what General Catalyst paid to stop selling software to hospitals and just buy the hospital instead. They set up a company called HATCo and bought Summa Health in Ohio. I don't know much about running hospitals. But I know enterprise sales. Selling software to massive organizations is pure agony. Founders get an initial meeting, think momentum is real, and spend eighteen months waiting on committees. Most startups run out of cash before anyone makes a decision. So General Catalyst took a different route. By owning the hospital, their companies can put software to work right away instead of waiting months for permission. Founders selling into almost any legacy industry run into that same wall. Endless reviews and layers of approvals quietly kill momentum. Building great tech is hard. Getting through the front door is usually what breaks you. Buying an operating business gives you an immediate place to implement and scale your tech, without spending years waiting on outside buyers. What industry do you think could stop selling and buy their customer instead?
-
Michael Lazerow shared thisJen Linn was fighting for her life in an Equinox studio across from our office. The movement she started 10+ years ago has now raised over $450 million. She was using that cycling studio to raise money for rare cancer research through Cycle for Survival. Our team was the first corporate team to ride. And we rode every year after that. Jen never made it about herself. She once told us that watching our company show up to fight the disease that would take her life was one of the most motivating things she had ever seen. That changed something in me. I wanted to do more. In August 2011, I put one sentence in bold on a slide deck in our board meeting: "Giving isn't a byproduct of great businesses. It causes great businesses to be built." The board thought I was crazy when I suggested that part of our revenue be donated to causes we care about. So, I lost that battle. I thought they were wrong then. I still think they were wrong today. Jen had already shaped our culture in ways no board vote could undo. Our team knew what we stood for because she showed us what showing up actually looked like. A year later, when we were selling the company. Google offered us $100 million more than Salesforce. We chose Salesforce anyway. Marc Benioff had built giving into Salesforce from day one. 1% of time, 1% of equity, 1% of profit. That alignment mattered more to us than a bigger check. I believe Jen had something to do with that decision, even if she never knew it. How have you built giving into the foundation of what you are building?
-
Michael Lazerow posted thisOne of the biggest shifts I had to make as a founder was realizing that my job wasn't to do more. It was to become crystal clear about the few things only I could do. The best CEOs don't try to own everything. They focus relentlessly on their core responsibilities and build systems for the rest. 1. Set the direction and protect your focus. As CEO, your attention is one of the company's most valuable assets. ↳ Every meeting you shouldn't attend. ↳ Every approval that could have happened without you. ↳ Every "quick question" that interrupts your day. It all comes at the expense of the work only you can do. Your job isn't to react faster. It's to think farther. Your team needs clarity on where you're going, what matters most, and how decisions get made. Without that, people don't become more independent. They become more dependent on you. One of the hardest lessons I learned is this: If you're solving everyone else's priorities, you're probably neglecting your own. Focus isn't a productivity hack. It's one of your most important responsibilities as CEO. 2. Protect the business. Growth is exciting. Profit keeps you in the game. ↳ Know your cash. ↳ Know your margins. ↳ Know how long you can operate if things slow down. As CEO, you don't just chase revenue. You build a business that's resilient enough to weather uncertainty. Hope isn't a strategy. Financial discipline is. 3. Build a team that doesn't need you for everything. The goal isn't to hire people who execute your instructions. It's to hire people who can make good decisions without waiting for permission. If every important decision still comes back to you, ask yourself why: ↳ Did you hire the wrong people? ↳ Or did you hire the right people but never give them enough clarity, context, or trust? Great people don't need constant oversight. They need clear expectations and the freedom to own the outcome. Here's a simple test. Look at your calendar. How much of what you're doing this week could someone else own if the right systems were in place? If the answer is "a lot," that's not a people problem. It's a leadership opportunity. Here's what I've learned: Your job as CEO isn't to be involved in everything. It's to make sure everything doesn't depend on you. The more your business relies on you, the harder it is to grow. The more it relies on great people, clear direction, and strong systems... The more freedom you create for yourself, your team, and your business. 👇 Which of these responsibilities deserves more of your attention right now?
-
Michael Lazerow shared thisI've sat in thousands of meetings. Most of them didn't need to happen. Here's the question I ask before I sit in one now: what kind of meeting is this? Most of the time, nobody can answer that. → Are we sharing information? → Are we gathering ideas? → Are we making a decision? → Are we assessing a project? Pick one. Trying to do all four in one meeting is how you end up doing none of them well. The meetings everyone dreads are usually explanation meetings dressed up as decision meetings. Someone updates the room for forty minutes. Everyone nods. Nothing gets decided. That's not a meeting. That's an email with a mandatory audience. I learned to ask the question before I send the invite, not during the meeting. A bad meeting doesn't just waste an hour. It trains your team to expect meetings that go nowhere. They stop showing up mentally, even when they show up in person. Every meeting you don't need is one less reason for people to tune out the ones you do. What's one meeting on your calendar that could've been an email?
-
Michael Lazerow shared thisYour competitor's AI team of 12 will outperform your department of 100. And they will do it at a fraction of the cost. At Buddy Media, every time we doubled revenue, we doubled headcount. More engineers, more salespeople, more offices, more overhead. That was the only playbook. You grew by adding people. I am watching companies right now that have broken that equation completely. They are generating the same output we needed hundreds of people for, with teams you could fit in a single room. The revenue scales, but the payroll barely moves. Here is why that matters: When your competitor runs with a tiny team, they keep way more of every dollar that comes in. Their margins are massive. That means they can charge less, build faster, and spend more to win customers. If you are paying a massive payroll to get the exact same work done, you cannot compete. You cannot hire your way out of this math problem. Most investors still value businesses using the old model based on headcount and old multiples. They have not realized yet that the companies using AI to run lean are going to swallow their competition. How are you approaching team size as AI tools get better?
-
Michael Lazerow shared thisStarting a company is an open invitation for people to watch you fail in public. You have to be a bit crazy to sign up for it. When you start building, you have to convince yourself you are capable of pulling off something massive on your own. You need that ego. You need the audacity to believe you can beat the odds when nobody asked you to try. Without that belief, you never leave the starting line. The paradox is that ego only gets you started. To actually succeed, you also have to be an empath. You need the emotional intelligence to reach out and listen. If you only listen to yourself, you ignore what customers are telling you, miss blind spots, lose employees and build something nobody wants. That is where the magic happens: The ego to do something on your own, combined with the ability to listen to others along the way. How do you balance self-belief with listening in your work?
-
Michael Lazerow shared thisThere will always be more you could be doing. There will always be more customers to chase, more products to build, and more ideas competing for your attention. Early in our careers, we learned that trying to pursue everything at once only made it harder to make real progress. The challenge was deciding what deserved our time and resources. This week's newsletter digs into how we learned to separate what matters from everything else competing for attention. 👇 Tap below to read the full story and see what deserves more of your attention right now.
-
Michael Lazerow posted thisBetting everything on an illiquid deal does not work. Nobody buys a single stock and expects a balanced outcome. Yet with startups, it is easy to hear an incredible pitch, get excited, and jump in. I have backed over 100 startups over 20 years. Here is what that lived experience actually taught me. Early stage investments are completely illiquid. Your capital is locked up for years. There is no selling when things get bumpy, and there is no quarterly liquidity. Most of the startups I backed returned nothing. Even with great founders, the majority of individual bets failed. My portfolio only worked because of portfolio math. The breakout winners had enough room to return everything else. Backing an illiquid startup in isolation is betting on luck. Without building a real portfolio of bets, the math breaks down before it starts. How do you approach portfolio math when backing startups?
-
Michael Lazerow reposted thisMichael Lazerow reposted thisI got hit by a car... Funny how the world works! A few minutes before that, I was leaving a dinner with Jeremy Sanchez where he gave me a copy of the book Shoveling Sht*t. Very foreshadowing. 🙃 Safe to say, the next day I found myself with both personal and business sh*t to shovel out of. I could barely take conference calls (jaw was wired shut like Kanye). My co-founder Fred Lamming didn't miss a beat, made sure Kiwi Data stayed on top of everything. The team went on to have one of our best months ever (in both sales and features released). There was a pretty good lesson in that. A lot of entrepreneurship is dealing with the problems, chaos, and unglamorous work that comes with building something. But if you’re building it right, you have a team to trust, and you play to your team's strengths. You shouldn’t be holding every shovel every second (e.g., "moneyballing" your team). Last week, the story came full circle when I ended up at a dinner with one of the authors and a great group of leaders in Chicago’s tech scene. I learned a lot from both investors and business owners about our experiences, gaps, and areas ripe for opportunity in Chicago and beyond. Thank you, Jeremy and Merraine Group, for bringing everyone together. And Kass Lazerow and Michael Lazerow — the timing of your book showing up in my hands, and the lessons learned, were uncanny and much needed. 📖 🥝
-
Michael Lazerow liked thisMichael Lazerow liked thisAn underrated cheat code in life: Beingeasy to work with. Show up early. Be kind. Do more than your share. Be reliable and consistent.
-
Michael Lazerow liked thisMichael Lazerow liked thisThe fascinating business story and facts behind Burberry!
-
Michael Lazerow liked thisMichael Lazerow liked this10/10 success habits that NO ONE is telling you about:
-
Michael Lazerow liked thisMichael Lazerow liked thisThe best business class I ever took didn't have a syllabus. It was decorating other people's homes for Christmas. I did it in college for money. It turned into a real business with repeat customers. A job teaches you one piece of a business. A side business teaches you all of it. → Can you get a stranger to say yes? → Can you find the next customer when the first one is done? → Can you charge enough to make it worth your time? → Can you fix it when it breaks, because no one else will? No class teaches you those. A few years later, I got asked to start a new web division from scratch. I had to build it and sell it on my own. Same skills as the Christmas business. Bigger clients. I never would have known I could run a business without running a small one first. What side gig taught you more about business than any class in school?
Experience & Education
Publications
-
The Dreamer’s Dilemma: Prevent Your Dreams from Turning into Nightmares
LinkedIn
See publicationIf you think your dream should come true and you’re not violating any rules of physics (or basic human ethics), go for it. Tune out the critics. Or better yet, turn those critics into the electric power to fuel your dreams, as Elon did.
-
When is it OK to bash a founder?
LinkedIn
See publicationSo why is it that some of my fellow entrepreneurs have no problem publicly attacking other business builders?
-
Why Weirdos Outperform Normals
LinkedIn
See publicationWe should teach our kids to be weird. Instead of trying to get our kids to fit in, we should help them celebrate why they are different.
-
Twitter's Ads API is Here: So What and Now What?
Ad Age
See publicationTwitter's ad APIs are a natural progression for the company. And, quite frankly, I expected it to come a bit sooner. Nonetheless, this is a game changer for brands who need the power to pull off real-time engagement that turns tweets and posts into memorable content.
-
Facebook Graph Search Is Here. What Do Marketers Need to Know?
Ad Age
See publicationWhile Zuck did not focus on brands, it's clear where Facebook is going with its search strategy. And businesses large and small will be one of the primary beneficiaries.
-
The Truth About Facebook Advertising
Fast Company
See publicationOur aggregate, quantifiable numbers, as well as knowledge of our brands' ad spend, show the speed at which brand advertisers are investing into Facebook. Companies that spent $1 million last year are spending $5 million this year. Companies that spent $10 million last year are upping spend to $25 million or more.
-
Social Media Advertising Is Set to Explode. Who Will Control It?
Ad Age
See publicationIn a world where the content is the ad and the ad is the content, the barriers between the different types of agencies go away, and all are frothing at all the new and growing revenue streams.
Honors & Awards
-
Leader of the Future Award
Frances Hesselbein Leadership Institute
-
#1: Silicon Alley 100
Business Insider
-
Ad Age Digital A-List
Ad Age Magazine
-
Crain's New York 40 Under 40
Crain's New York Business
-
Ernst & Young Entrepreneur of the Year
Ernst & Young
-
Fortune Magazine 40 Under 40
Fortune Magazine
Recommendations received
15 people have recommended Michael
Join now to viewOther similar profiles
Explore more posts
-
Rob Frasca
Frasca Executive Dispatch | Wednesday: AI (Enterprise / Leadership) At Affinnova we used genetic algorithms to help Fortune 500 brand teams choose packaging and product concepts. The algorithm was never the hard part. The hard part was persuading a brand group to let the result overrule a call it had owned for a decade. The clients who changed who signed off got the value. The ones who kept the old sign-off got a very good report. 1. OpenAI released GPT-6 Sol and Luna on 22 September and cut API prices in half against the previous tier. The company says the new rates are permanent, not introductory. Frontier-grade reasoning just became a line item a procurement desk can approve without a meeting. 2. The same day, The Information reported that Amazon, Microsoft and Figma are discounting or bundling AI features to hold customers. FICO's CIO, Mike Trkay, said dozens of his vendors have added AI at no extra cost at renewal, and that a contract charging separately for it is one he would no longer sign. 3. A PYMNTS Intelligence study published the same day found that firms with AI embedded narrowly and firms with it embedded widely use it on roughly the same number of tasks. The returns diverge anyway: 55% of the narrow group report one, against 93% of the wide group. The deep adopters also report nearly twice as many barriers. They are not finding fewer problems. They are finding more of the company. What this rhymes with: Affinnova. The optimisation was for sale. The willingness to act on it was not. Second-order effect: when every competitor rents the same intelligence at the same falling rate, the model stops being the differentiator. Decision rights, clear ownership and an approval path that does not assume a person retyping data become the advantage. For institutions: stop benchmarking which model you bought. Ask which decisions it is allowed to make, who changed their sign-off to let it, and what your operating plan assumes about the cost of intelligence. AI doesn't replace experience. It compresses it. — Rob Frasca | COSIMO Digital | cosimodigital.com Capital markets, rebuilt on-chain, amplified by AI #EnterpriseAI #AILeadership #FutureOfWork
-
Mary Grove
At Bread and Butter Ventures, we're in our 7th year of investing in digital health. I've been hearing a lot of feedback lately from both funds and founders alike that VC funding for tech-enabled care delivery is fewer and far between these days. I'm super bullish on tech-enabled care as a component of a digital health portfolio because I believe that true, lasting innovation will be driven by bottoms-up early stage innovation responding to top-down industry pain points, and that to innovate we must have distribution through the incumbent plumbing of the healthcare system - and that includes care at the center. Yes, the margins are lower than pure software, but the distribution network of healthcare is very different than pure B2B. We're super interested right now in: ✅ Applications of AI to in infrastructure and operations of health care systems, provider networks, health plans to reduce manual work and enable everyone to operate at their best and highest use ✅ Applications of AI to clinical decision support and ultimately care delivery ✅ Solutions that address population health and help with access to care in both rural and urban settings (both from a care & cost perpspective), cardiometabolic health, women's health (still wildly uninvested opportunities to serve half the population), eldercare ✅ Insurtech, fintech and the payments layer of healthcare We would love to connect with more co-investors at all stages (pre-seed, seed, later stage) who are actively investing in digital health and specifically at tech-enabled care solutions to drive the next generation of healthcare innovation. Please DM us or tag a firm/investor here!
48 Comments
Explore top content on LinkedIn
Find curated posts and insights for relevant topics all in one place.
View top content