Category: Uncategorized

  • Small Steps

    Big changes come in small steps. The key to success in achieving big things is breaking them down into small pieces and making steady progress over time.

  • Navigating 2022 Layoffs: Founder’s Poll Results and Recommendations

    May 2022 had more layoffs than March 2020 at the start of the pandemic, and June is on pace to ellipse May. The tech boom that started after the 2008 crisis is now over, and we’ve entered the part of the downturn where layoffs accelerate.

  • Working backwards from Winning

    Startups win by growing fast. As Paul Graham’s startup = growth essay explains, “A startup is a company designed to grow fast.” VC-backed startups are designed to “eat capital and shit growth.” Growth expectations create a new definition of winning at each round of venture capital that your startup raises. Most businesses can’t scale rapidly based on…

  • Three Pillars of Leadership: Vision, People, Execution

    Leadership teams are built on three pillars: vision, people, and execution. The team needs to be strong in all three and this is achieved by thoughtfully designing for overlapping and non-overlapping strengths.

  • How to Build Founding Teams That VCs Want to Invest In

    Introduction No VC pattern matching is more well honed than the assessment of founding teams. Last year I surveyed a list of top VCs on what they think are the three most important aspects of successful founding teams.  The top three that came back were: I compiled all the responses into a founding team builder.…

  • Startup Investment Memo Template

    Introduction A well written memo is the core of sharpening your startup pitch.  You should write the memo first, and build the deck only once you have a final draft. Many funds write investment memos internally for investment committee meetings, so when an entrepreneur writes one they are effectively seeding what will be shared directly…

  • Timeblocking: Calendar Scheduling and Time Management to be Happier and More Produtive

    Introduction Everyone wants to maximize productivity and work-life balance with better calendar management and scheduling. Over the years I’ve learned two key tricks. First, plan with the calendar instead of a task list because the calendar controls real life time allocation. Second, manage inbound and meetings within predefined calendar blocks instead of reacting, because calendar…

  • Market Mania; The Top Ten Books on the History of Bubbles, Manias, Panics, and Crashes

    Summary of our current place in the market cycle We’re at the tail end of an awesome tech cycle with massive real value creation. This was the real dot-com boom. The information revolution created this weird self-Heisenberg effect where information about the market travels so fast that markets get way ahead of economics then collapse…

  • Hiring For Startup Fit

    I’ve hired three CEOs, dozens of executives and managers, and hundreds of employees into early stage Seed and Series A stage startups. I’ve been exposed to hundreds of early stage teams through my network and the startups I’ve built in Consumer, SaaS, Enterprise, Deep Tech, Biotech, Fintech, Agtech, and other markets. So I’ve seen a…

  • How to Hire Your First Leaders and Clean Up When You Get it Wrong

    You made it! Your startup has some early traction and now you’ve hired your first leaders to help grow the company. Trouble is that things aren’t going as planned. Some parts of the company have team members that aren’t up to the bar you initially meant to set. These same parts of the company aren’t…

  • How to Find the Right Co-founders and Build the Best Founding Team

    Building the founding team is by far the most important part of building a startup. The founding team sets the vision, builds the rest of the team, builds the prototypes, and brings in the initial customers. Once you have one or two people that want to work on a startup, there can be a tendency…

  • A System for Achieving Your Goals in 2021

    Setting goals is a lot more common than achieving them. This is in part because of how we set our goals, and in part because of how we check-in on our goals and hold ourselves accountable. It’s important to know why we’re setting goals, so that we have a sense of commitment and motivation to…

  • B-Player Execution Is Allergic to A-Player Leadership; Identifying B-Players and Transitioning Them Out

    We all know the old “B-players hire C-Players” mantra, but maintaining an A-Players-only team isn’t easy. The #1 mistake A-Player leaders make is failing to identify and transition out B-Players quickly enough. A-Player leaders get a lot of fundamentals right, but invariably make mistakes and hire some B-Player leaders who have an amplified effect and…

  • The Professional Hierarchy of Needs: Happy Teams are Winning and Growing

    You can try to win, or you can try to make people happy, but you can’t do both Paradoxically, trying to win leads also to making people happy, because people are happy when they win. Trying to make people happy in ways other than helping them win ends up making them unhappy, because they are…

  • Keepin’ the Dream Alive: Realistic Startup Milestoning for Fundraising and Profitability

    Until startups are profitable while growing, they are burning down cash against a finite runway that’s usually less than two years away. As a result, it’s important to have a realistic plan at all times for what it will take to i) raise additional capital, ii) become profitable, or iii) fall back to m&a or…

  • JMTI: Just Make the Intro

    Double opt in intros are obsolete and too slow for the pace of modern business. Just make the intro.

  • Scaling Engineering Teams With Distributed Ownership

    After 20 years leading engineering, product, and as CEO, and nearly 15 years working in the bay area with the best engineering leaders in the world, I’ve come to appreciate how quickly management culture has evolved in the past decade, and how little has been written about the operating details of practical modern engineering management.…

  • Cracking the Crux of the Mortgage Market

    Mortgage banking is a huge market, but it’s been a notoriously bad market for startups. Late-funnel-high-intent keywords for real estate are among the most lucrative and efficient in online ads. So the only real way to build a great business is to find a more cost effective way to scale acquisition. One approach is to…

  • The Big Bang Launch vs Dialing in the Vision

    Startup CEOs and Product leaders often fancy themselves as Steve Jobs types, launching the iPhone on stage to a wave of shocked and adoring applause. When startups conflate the destination (the marketing launch) with the journey (the product build), we call it the Big Bang Launch. Big bang launches are ineffective because you aim to…

  • Series A CEO: Building Management Teams and Breakout Commercial Traction

    PM fit, or zero to one, is an important but murky concept. I think that ‘one’ is supposed to refer to ‘repeatability of sales’ in the case where there is  a clear product that meets a market need and scales well enough to create a venture-backable startup. ‘One’ can also refer to the first anchor…

  • Vertical AI Startups: Solving Industry-specific Problems by Combining AI and Subject Matter Expertise

    Low level task-based AI gets commoditized quickly and more general AI is decades off. In the meanwhile, will new AI startups succeed or will the value accrue to Google, Facebook, and Amazon? While most of the machine learning talent works in big tech companies, massive and timely problems are lurking in every major industry outside…

  • Five AI Startup Predictions for 2017

    With AI in a full-fledged mania, 2017 will be the year of reckoning. Pure hype trends will reveal themselves to have no fundamentals behind them. Paradoxically, 2017 will also be the year of breakout successes from a handful of vertically-oriented AI startups solving full-stack industry problems that require subject matter expertise, unique data, and a…

  • How Socially Aware Leaders Win: The Field Guide to Social Intelligence

    This guide aims to present you with an easy way to understand and apply empathy better. It will hopefully be useful to everyone, and is written especially for leaders. We start with an overview of emotional and social intelligence, and end with an audiobook workout routine. Emotional and Social Intelligence Much has been written about…

  • Machine Learning vs. Quants: The Advantages of Machine Learning in Finance

    As quantitative finance has matured and the importance of computation has exploded, it’s time to use machine learning to harvest the new low hanging fruit. Traditionally, quants might work alongside engineers and computer scientists — the quants provide the statistical expertise, and the computer scientists and engineers provide the computational expertise. Machine learning folks combine…