History doesn’t repeat itself, but it certainly rhymes—or so the saying goes. For entrepreneurs, I believe 2021 and the years to come will rhyme with 2007. Froth Rhymes In 2007, I worked in leveraged finance at a top Wall Street investment bank. When I started my job, it was so busy that I could barely…
Fundraising Tips for Early Stage Founders
As a former startup founder, I was often unsure about best practice for proactively communicating with investors ahead of my next round. Now sitting on the other side of the table as an investor, I wanted to share my thoughts. Here are five tips I recommend for early stage founders gearing up for their next…
The Gratitude Algorithm
There’s a lot of fluff written on gratitude, and it’s easy for those trained in engineering (including myself) to be readily dismissive and miss out on something transformative. So I wanted to write an article addressed specifically to hackers and engineers – starting from first order principles of experience, and providing a heuristic to transform…
Health and Wealth for Retirees: A Compelling Startup Opportunity
I believe there is a massive opportunity to build a startup that helps retirees manage both health and wealth. About 10,000 Americans turn 65 every day. Most enter this critical period of their lives with fear and uncertainty, and more often than not, piecemeal guidance that covers just healthcare or financial decumulation. Moreover, many companies…
GovTech SaaS: Navigating Unfair Advantages and Perils
I love finding opportunities to invest in startups that have massive financial potential and also strengthen the financial fabric of society. GovTech SaaS is one such opportunity. In future articles, I’ll cover opportunities in other sectors. I believe GovTech SaaS businesses have unfair advantages that make them some of the most interesting and underrated opportunities…
Shoes in Auschwitz: Regaining Perspective on the Anniversary of World War II
Today (September 1st) is the anniversary of the start of World War II. This article is dedicated to Dr. Edith Eger, a Holocaust survivor whose remarkable life story—poignantly told in her memoir The Choice—is a testament of the power to choose light and hope, even in the depths of unfathomable darkness. These days, it’s easy for…
The 10 Essentials of a Venture Scale Company
This article is focused specifically on venture-backed startup CEOs and leaders (rather than small- and medium-sized businesses not focused on raising venture capital.) Here are what I believe are the 10 most important attributes of building an extraordinary venture-scale business. 1. See the world differently This means being a contrarian in an established market or…
Capital as a Service: The Next Fintech Startup Opportunity
The global lending market is massive. In the U.S. alone, small businesses borrow over $600 billion annually and banks hold over $1.5 trillion in consumer loans. Yet despite market size, building a profitable, scalable lending startup is challenging because it requires running a capital markets business in addition to running one’s core business. Take LendingClub…
Highest Contribution Entrepreneurship: 3 Questions Every CEO Should Ask
The keys to sustained success of every great company can be distilled down to three questions. Highest Contribution Strategy Question #1: Are we as a business working on our highest contribution strategic initiative? Amazon won the battle for the world’s biggest online book store before the company won the right to build Amazon Web Services….
Dropping Into Wonder Before Dropping Into Work
Lost in a Powerful Virtual Reality Headset Picture the scene: the pandemic is over and you find yourself at CES in Las Vegas. You enter the crowded floor and a shiny device in the center of the room immediately grabs your attention. It’s the most sophisticated virtual reality headset that has ever been invented. You…
Why Life Insurance Should Look More Like a 401(k)
You Don’t Need It Until You Need It I am a genuine believer in the value of life insurance. It’s a product that, when priced fairly, is invaluable. In the case of someone close to me whose mother passed away during his youth, this product was the only reason his family was able to keep…
Love or Fear in America: Learning from Germany, Singapore, and Israel
“Between stimulus and response there is a space. In that space is our power to choose our response. In our response lies our growth and our freedom.” – Victor Frankl We each face a choice in every single moment: to act from a place of love or fear. Fear wins by default, and for good reason….
The Robo-Advisor Escape Velocity Conundrum
Escape Velocity for a Mass Affluent Wealthtech Startup The robo-advisory industry has massive market potential, which is measured in the trillions in assets under management (AUM) in the United States alone. However, few tech startups will make it to the threshold I refer to as “escape velocity,” that is, building a large, independent company with…
Common Ground: A Founder’s Inner & Outer Worlds
Going forward, I will generally write alternating articles that cover the inner and outer worlds of being a startup founder. First Be, Then Do It is my goal to help build what I’m calling “common ground” for a better world. This first requires getting the “being” aspects of a human being right, and then taking…
The World I Want to Build: Dinner With Warren Buffett, An Ovarian Lottery, and COVID-19
The Ovarian Lottery Years ago, I was fortunate enough to have dinner with Warren Buffett. I vividly remember his observation that everyone at the table had “won the ovarian lottery.” In other words, each of us had been blessed by fortune simply by the circumstances of our birth. We took for granted our access to…
Inside & Out: A Framework for Startup Recruiting, Sales, and Fundraising
I recently spoke on a panel to help tech professionals find jobs in the era of COVID-19. I realized that the system can be extended to fit a wide range of startup use cases – from recruiting at scale, growing sales, fundraising – or any activity that involves optimizing a network of contacts. It involves…
Joining Jackson Square Ventures: Helping Founders Create Change
On my 21st birthday, I sat on a beach and meditated. I focused on the question “What should I do with my life?” The answer that came was “Create change”. Call it a quarter life crisis 🤷♂️ A few months later, an opportunity arose to put this into action. My Israeli great-aunt was killed by…
Failing Is a Feature
As the year draws to a close, I find myself intuitively wanting to release the excess baggage of the year – all my moments of failings, longing for what could have been, regret for mistakes I made, and unfulfilled yearnings. With this natural process of letting go, it’s tempting to add a tinge of guilt,…
Choose Good
Our decisions shape our realities. Getting this right is crucially important – as an entrepreneur, leader, parent, friend, partner, or just plain-old human being trying to get by. Left to our own devices, we are driven by unconscious patterns learned from childhood. As children, we watched and learned from our parents, and this dug deep…
Death as a Business Mentor
A unique feature of being human is finding oneself in a contracted or open state of being. Your flight has been delayed, you’re late for a meeting, or worried about closing a critical deal. As a result, you’ll likely find yourself in a contracted state: clenched, tight, and with a generally negative outlook. As a…
Why I Make Every Day a G.E.M.
The Buddha famously said that “All of life is suffering”. As heavy as that sounds, it’s not necessarily a recipe for unhappiness. Regardless of what line of faith (if any) you adhere to – we all share a common human experience. More often than not it is one of suffering and pain – which we…
A Call to the Living
This week I was struck by how powerful of a tool death is in shaping our lives. Last Monday night, I saw a friend of mine in the ICU, holding on to life via a breathing tube. He was in an induced coma but I was struck by how vital he still looked. He was…
The Perfect Work Day: Dump Goals, Embrace Systems
Happiness is always “just around the corner” Growing up, I was taught that goals are sacrosanct – to set big ambitious ones, and work tirelessly to reach them. Implicit in this approach is a recipe for unhappiness. We tell ourselves that we will be happy only when this goal is achieved – and not along…