After a certain threshold, the type of success you have is a choice. On one extreme there is Bill Gates. If he was purely driven by money, he could be the richest human on the earth, but he has donated over $50B to charitable organizations throughout the past 30 years. As a result, Tesla CEO and visionary, Elon Musk, recently passed him in net worth. While no one is questioning Gates’ success, his decision is similar to many who find early success, although at a much smaller scale.

The Movie Night assignment illustrated this concept for me, as I compared…


When I interned in early-stage venture capital, I looked at my fair share of pitch decks. Although my firm wasn’t on Sand Hill Road, I did see a lot of the classic team consisting of an ex-FAANG CTO and an Ivy League to Wall St. CEO trying to capture just 1% of some trillion-dollar market, claiming to be the Uber/Amazon/Air BnB of X industry.

I even looked at a company founded by an ex-NASA employee who literally studied rocket science. Startups are not rocket science; they are much more than that. …


Coffee might only be for closers, but venture funding goes to networkers.

You are the sum of the five people you spend the most time with, as the old adage goes. There is no industry where this is more true than in entrepreneurship.

Venture capital, especially at the early stage, is the business of judging people on their ideas and connecting them with others. When a startup founder goes to pitch a VC for funding, they hope that the ultimate outcome of a pitch is to secure funding from the angel/syndicate/fund to which they are pitching. Still, a successful pitch…


If a startup scales outside of the proverbial garage, hiring decisions are some of the most important a founding team must make. Paul Graham notes that it is tough to find independently-minded talent in the pipeline, due to its rarity. An equally as tall a task is to keep the same culture in a 50 person team as it was in the beginning with 3 founders and a box of pizza.

This fear is what kept McDonald’s a single store in San Bernardino (before Ray Kroc came along). However, as we learned from Ted Lichtenberger, it is possible to keep…


Every analyst in banking has gotten this dreaded email from a senior member at the firm, with a slide deck chalked up with comments sloppily written with an Apple Pencil attached. The deck is marked up with excruciating detail, mostly on font size, object alignment, and other formatting errors. In investment banking, every detail matters, to the pixel. Every cell and assumption in a model must tie out.

In an early-stage venture, projections are not worth the excel doc they are written on. A perfectly formatted deck might wow some investors, but one could argue meticulously pouring over documents is…


A classic debate in entrepreneurship is the jockey vs the horse — the founding team vs the idea. A great startup has both, but which is the better indicator of success?

Conventional wisdom says to bet on the jockey (founder). An A+ founder can execute a B idea, whereas even the best idea in the wrong person’s hands can never get off the ground (see: The Social Network). An idea is not a company, no matter how great that idea is.

Still, even the best founding team needs to be working on something large enough, interesting enough, and potentially profitable…


When we were effectuating our concept for E-Cup, the biggest hurdle we found was the legality of our platform. Certain Internet Service Providers (ISP’s) explicitly prohibit the resale of broadband (AT&T, Comcast, Verizon), others only explicitly prohibit the sale/share of physical equipment (Cox and Charter Spectrum).

Since our concept is a pure software play, we should only run into legal issues with the first batch of ISP’s and not the second. We could have limited our scope and not included AT&T, Comcast, or Verizon in our target market, but instead, I spoke to an industry expert at one of those…


A startup is an investment. This much is obvious. For a founder, it is an investment of time, money, network, basically an entire 3–7 years of one’s life. The decision to jump off the deep end and devote your life to a startup is a daunting one. The potential founder should have a concept, effectuated it, spoken to potential customers, and have deep knowledge of the industry. If all of these are in place, it might be time to quit the day job and take the leap.

Even with all of these ingredients in place, the startup might fall on…


The size of the market might be the most important part of a start-up aside from the founding team. Perfect execution and a great product can only take you as far as the number of people willing to pay for it.

Still, take a start-up that is in a huge market with the right team. Where do you go from there? You can’t build it and expect a trillion-dollar market to adopt it, even with great marketing. You need focus. You need to segment your market. The first segment a founding team should attack is their beachhead. A beachhead is…


WeFi was born on a Zoom call, where Matt, Cameron, and I were brainstorming a concept for our E-Cup pitch. Matt and I were in the same room as we live together, but our WiFi kept cutting out. When we finally reconnected, it became clear that we should try to solve our biggest and most obvious problem in fall 2020 — WiFi connectivity issues.

I have always been fascinated with marketplaces and their ability to solve a problem for two separate parties at the same time (both supply and demand). WeFi is a marketplace, but with a wrinkle — all…

William Omberg

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