Why understanding your values will help you select the right investor (or connect to the right founders)

This weekend I had a great conversation with a young, wise, and driven founder. It was a follow-up call that didn’t focus so much on the startup’s traction or how he was planning to expand to new markets. We discussed his ideal profile for a Head of Business Development. A few sentences resonated with me because he clearly described the desired characteristics in people who become involved in his venture — no matter if the individuals are employees, advisors, or investors.

The founder shared four specific qualities he seeks out to propel the startup into a transformational multi-billion dollar company…

Crafting a solid narrative is an essential skill offline or on.

I typically don’t have a planned content calendar when I look to publish a post every Wednesday (that may be a good or bad thing). Sometimes I look to elaborate on a thesis that I’ve written. But many times, I try to reflect on a motif that has repeatedly been shared with me the prior week, which makes me think of my parents. Each of them had a different style to the content they developed for their respective professions. My mother, a teacher, always lesson-planned months — maybe quarters — in advance, while my father, the pastor, outlined his sermons…

The evolution of data tools presents an opportunity for functions outside of engineering to get applications that help them make better, faster decisions.

Two trends over the last ten years have intrigued me: 1) As software continues to eat the world, the importance of the engineering function has increased significantly, and 2) corporates (from all industries) increased interest in capturing and leveraging data to improve operations. These two separate shifts have produced impactful SaaS/cloud companies, as well as a need for solutions that optimize enterprise companies’ most precious resources — engineers and data.

To preserve the first asset, engineers, companies (CTOs or engineers themselves) have sought the developer and operational tools available. DevOps companies increase efficiency, improve quality, and reduce costs for designers…

A response to my June 2020 post.

It’s Wednesday. So it’s time for me to share what trends or concepts are occupying my brain. Last week I wrote about how insane the VC market has been thanks to more capital in the market, low-interest rates, and phenomenally startups that are increasing the acceleration of technology adoption in many industries. The moral of last week’s post was to stop complaining and adjust to the game (speaking directly to myself).

I later saw that the “State of Venture Capital” presentation from the “All In” Podcast further elaborated that the times are changing. …

Why 90s NBA is to the 2010s VC ecosystem as the 2020s NBA is to the 2020s VC ecosystem.

Last week, I had a great conversation with a friend who had just transitioned from a tech operating role to an early-stage investor role. When I asked him how it feels to be in the venture: he stressed that he felt very fortunate and that it was an intriguing time to enter the venture capital. He is at an established early-stage firm, and I asked if the current funding environment has caused his partnership to shift their strategy or not.

He told me the best quote I heard all week. He said his partners have stressed that you have to…

I’ve always been a contrarian (which reads less contrarian when you type it out). Better yet, I like to take the path that others around me think is harder or less transparent. It’s a way of life that has added some stress ( and a few grey hairs🤫), but the reward has outweighed the obstacles (💪). Anyway, this thinking has led me to scour eyes 👀 North America for founders looking to disrupt legacy or old-school industries.

Of course, I’m looking for pure enterprise SaaS and AI tools. Still, the startups that intrigue me (and typically 😴 others) are those…

If 2020 taught us anything, it’s that VCs must shift their focus towards America’s essential industries.

Over the past two decades, we’ve lived through two recessions, not including the present crisis. Living through one crisis while still reeling from the prior feels a lot like staring into a rearview mirror while also focusing on the even bumpier road ahead.

In high school (better yet, it was college for the elder Millennials) when the dotcom bubble burst in the early 2000s, we saw a limiting truth emerge — online businesses were far more susceptible to failure than we initially thought. Most companies were chasing the popular trend at the time (e-commerce). Few took the opportunity to look…

Moving from a discount to e-commerce shopper mindset as an investor

I started my career on Wall Street in July 2007. So my first months of working introduced me to the possibilities of a bear market. At the time I was working as an equity research associate covering the REIT market, a sector that had outperformed the S&P 500 for the prior five years — until I got there. The Great Recession taught me early in my career that no matter how big a company is (or how long it has been any industry leaders) can disappear in an instance…remember Bear Sterns or Lehman Brothers? In Equity Research, I was repeatedly…

A few words about GreatPoint Ventures’ investment in KlearNow

When I joined GreatPoint Ventures in January, I was really excited to work with a team that sought to support revolutionary entrepreneurs across a diverse array of industries.

Because, for the past 3 years as an investor at Prologis Ventures — the investment arm of the world’s largest industrial real estate owner — my role was to invest primarily in just three verticals: commercial real estate tech, logistics & supply chain tech, and industrial IoT.

Ironic then, that my first deal at GreatPoint would throw me right back into one of those core areas — logistics.

As it turns out…

Excerpts from Endeavor’s Multiplier Effect Podcast

Two weeks ago I was invited to Endeavor’s “Multiplier Effect” podcast to give my personal perspective on shifts I’m seeing in the VC and startup ecosystems as well as some tips on how entrepreneurs can successfully identify investment partners during these unprecedented times.

Below is an excerpt from the podcast that focused on how both VCs are evaluating opportunities and investor characteristics founders should consider in this market. Thanks to Canem Arkan for having me on the podcast. You can find the entire episode below.

How VC’s and Founders can evaluate opportunities in this market

[Canem Arkan] You’ve said several things I really want to go back and touch…

Earnest Sweat


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