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  • Everyone told me it would be lonely at the top. 07/02/2026
    They were half right. There is a specific kind of solitude that comes with the role. Decisions that land on your desk at midnight with no one to share the weight. Conversations you can’t have with your team because the wrong word at the wrong moment shifts culture in ways you can’t undo. Board rooms […]
  • The AI Governance Question Every Board Is Avoiding 06/25/2026
    Boards are fielding more AI questions than ever. In the past year alone, the volume of AI-related agenda items has surged across industries — and that trend shows no sign of slowing. Most of the conversations I see stay stuck at the technical layer: model types, data privacy architecture, vendor security certifications. These aren’t the […]
  • Raising money is easy. Deploying it wisely is the hard part. 06/18/2026
    Here’s what 30 years of angel investing taught me about capital strategy. Over the years, I’ve watched brilliant founders raise millions, then burn through it on growth experiments that never had a real chance of paying off. They mistook motion for momentum and confused speed with clarity. Expensive hiring plans, premature expansion, and oversized marketing […]
  • Are you wasting money filing patents? 06/11/2026
    I’ve been working with early-stage companies, and their intellectual property protection plans for years. But only recently I read a clear document on the risks and rewards of patent strategy.  Thanks to Russ Krajec, a patent attorney, for the quick improvement in my education, here are some important points to consider when thinking of your […]
  • In the age of AI, a hiring plan or better execution strategy? 06/11/2026
    For a few years, calling it a growth strategy mostly meant writing a hiring plan. More engineers. More sales reps. More headcount filling in the gaps between where you were and where you said you wanted to be. That worked when capital was cheap enough that the plan could outrun the question of whether it […]
  • The biggest valuation mistake founders make isn’t aiming too high 06/04/2026
    It’s believing the number means something. I’ve valued 100+ early-stage companies. Created a framework (the “Berkus Method”) that’s used globally. Here’s what five decades taught me about startup valuation: Your pre-revenue valuation isn’t a prediction. It’s a negotiation. VCs know this. Founders often don’t. They walk into a room believing there’s some objective truth to […]
  • What smart advisors taught me 05/28/2026
    The single best decision I made early in my entrepreneurial career wasn’t about product or market. It was asking smarter, more experienced people to sit beside me. That’s what an advisory board does. And unlike a formal board of directors — with its governance requirements and legal obligations — an advisory board is a smaller, […]
  • What if your leadership decision is unpopular? 05/21/2026
    It will happen. More than once. Probably more than you expect. The moment arrives quietly, you’ve weighed the data, consulted the right people, and landed on a decision that you know is correct. Then you look around the table and read the room. Crossed arms. Flat expressions. Polite silence where enthusiasm should be. Here’s what […]
  • The average successful founder is 42 years old.  05/14/2026
    Not 24. Not fresh out of a dorm room. Not someone who’s never felt the weight of a payroll they weren’t sure they could make. The mythology of the young founder is real — and it’s misleading. It selects for a very specific type of company (consumer tech, social, gaming) in a very specific window […]
  • Over-valuation!  The investor’s nightmare 05/07/2026
    Nothing kills an early funding conversation faster than a number that makes an experienced investor raise an eyebrow. I’ve sat across from many hundreds of founders over five decades. The ones who walk in with a $10 million pre-revenue valuation and a confident smile — but no methodology behind it — leave without a term […]
  • Three times a flight home in silence.  A VCs lament. 04/30/2026
    Three times a founder for which I negotiated the sale of his company looked a buyer in the eye at the final moment before signature and said, “No. Changed my mind.” No warning. No discussion. Just no. Let me tell you three short stories. The first was my very first early-stage investment. A music technology […]
  • The Cash Flow Problem No Amount of Fundraising Can Solve 04/23/2026
    As an early-stage investor and board member, I have watched CEOs raise  millions of dollars. Here’s one memorable case: One of “my” companies raised three million from an early-stage VC firm.  Six months later, he was out of cash and begging for bridge financing. His investors were furious. “Where did the money go? You said […]
  • Should we use AI for critical negotiation? 04/16/2026
    Would you walk into a negotiation with an AI as your advisor and negotiation partner?  What if I told you your AI advisor would be running scenario analysis in real time? The thought of that will change how I think about negotiation preparation forever.  It was the subject of a recent monthly CEO roundtable where […]
  • My personal stories of liability insurance 04/09/2026
    A CEO asked me during a board meeting whether he should drop his business liability insurance to save cash. His exact words: “What are the actual odds we’ll ever need it?” I had personal experience relating to his question and wanted to share it. But first… I quickly found online a photo of a building […]
  • How much information should you share with your banker? 04/02/2026
    I watched a CEO lose his credit line because he shared too little and then the banker asked for financial statements being shocked by the reduced profits and high liabilities.  And I watched another CEO lose his credit line because he shared too much of the wrong things with his banker. Both made the same […]
  • How about older board members in a young company? 03/26/2026
    There’s a debate happening in boardrooms across Silicon Valley that I think is being framed completely wrong. The question isn’t whether older board members can keep up with fast-moving tech companies. The question is whether you can afford to build a board without them. The instinct to load a tech board with 35-year-olds is understandable. […]
  • Only 23.4% of startups survive to the five-year mark. 03/19/2026
    Let that sink in. Track 100 startups today, and in five years, fewer than 24 of them will still be standing. But here’s what the headline number misses — it’s not random. The failures follow a pattern, and patterns can be broken. After decades of investing in and advising startups, I’ve watched the attrition happen […]
  • Are you willing to cannibalize your best product? 03/12/2026
    This one is tough.  I watched helplessly years ago as a young company with new tools and a newer user interface took the worldwide leadership position from our company in just a few years.  Ouch!  As more recently I sat on a board where the CEO refused to build what customers were asking for. His […]
  • Product-market fit isn’t a finish line. It’s a moving target. 03/05/2026
    I’ve watched many founders celebrate “achieving PMF” only to see their growth stall six months later. The market shifted. Customer expectations evolved. Competitors adapted faster. Here’s what five decades of investing has taught me about product-market fit: It’s not binary. You don’t flip a switch and suddenly have it forever. Real PMF shows up in […]
  • Ever Receive Worthless Advice? 03/03/2026
    I recently watched a young CEO assemble an advisory board. Six people. All smart. All experienced. All were willing to help. Several months later, he was more confused than when he started. One advisor told him to raise money immediately. Another said to stay lean and bootstrap. One pushed for enterprise customers who would pay […]

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