I’m not saying the bull run is over, but just in case…

Like everyone else who watches the news, we too have heard about the yield curve inverting, raising the question, “Is this finally the end of a ten year expansion?” Also like everyone, we don’t know. What we do know is that there is a greater level of risk to the economy than there was 6 … Continue reading I’m not saying the bull run is over, but just in case…

Inside the inside round

I’ve had two conversations about inside rounds in as many days – one with a portfolio company and another with a company outside of our portfolio. Both are entrepreneurs that I admire, have known for years and with whom I can be honest. These conversations made me realize that entrepreneurs have little window into the … Continue reading Inside the inside round

Okay, so what’s the number?

I often have conversations with founders that go as follows: Me: That sounds like terrific progress with customers and revenue, how does churn look? Founder CEO: A number of our customers are upselling very quickly and they all love the product. Me: Excellent, and how does that net out in churn? Founder CEO: We also … Continue reading Okay, so what’s the number?

Seed, speed, and we’re still here: my first decade in venture

December will mark a decade for me in venture. I didn’t start full-time, but it was nearly ten years ago that I landed an internship with a small fund in Chicago and “screened” my first startup story. I was a first-year business school student with a flip phone. A year later when I graduated, only … Continue reading Seed, speed, and we’re still here: my first decade in venture

SaaS: How will your 10th sale be 10 times easier than your first?

There was a period early on when we called ourselves a SaaS fund, playing just slightly on the “me too” side of the biggest trend of the 2000s, the saasification of software. We have since honed our message, but in those earliest of days, being a SaaS entrepreneur or investor was differentiating. Fast forward more … Continue reading SaaS: How will your 10th sale be 10 times easier than your first?

It’s 6:30pm. Do you know where your team members are?

Remember when it was just the five of you – three co-founders and two devs? You were flying from city to city knocking down your first few big contracts. Every Uber ride and hotel night was a flurry of emails with your co-founders – COO and CTO – implementing your first few customers and steering … Continue reading It’s 6:30pm. Do you know where your team members are?

New Year Letter

As a kid, I remember a pile of holiday “update” letters on our sideboard during the Holidays. People wrote in depth about their year, positive milestones for their family, and bumps in the road too. These notes were personal, genuine and from a bygone age – before smart phones, texts and even e-mail. Few write … Continue reading New Year Letter

Why Tesla will never be Apple

I regularly argue with my partners about how amazing Tesla is or isn’t. We all agree Tesla’s technology and product are a leap forward, but the question is whether the company will become a significant or even dominant worldwide auto player (and justify its orbital valuation).  Despite its buzz, Tesla has only a bit more … Continue reading Why Tesla will never be Apple

Moving a startup from bottom third to top third (it’s the people, silly)

The common wisdom of venture is that you lose all your money in the bottom third of your companies, score singles to triples in the middle third, and drive the vast majority of value in your top third. A “Midas Lister” we know astutely refines this saying, “It’s actually the top third of the top … Continue reading Moving a startup from bottom third to top third (it’s the people, silly)

Meet eTurns: Marshalls + eCommerce Returns

I am a Marshalls shopper. For most utility purchases ranging from socks to sheets to olive oil, Marshalls is my go-to. I am not alone. My regular visits see a line of 10-20 shoppers (often families) waiting to check out against a long row of 5-10 cashiers, all ringing up $X00 basket sizes. With TJX’s … Continue reading Meet eTurns: Marshalls + eCommerce Returns

Meet eTurns: Marshalls + eCommerce Returns

I am a Marshalls shopper. For most utility purchases ranging from socks to sheets to olive oil, Marshalls is my go-to. I am not alone. My regular visits see a line of 10-20 shoppers (often families) waiting to check out against a long row of 5-10 cashiers, all ringing up $X00 basket sizes. With TJX’s … Continue reading Meet eTurns: Marshalls + eCommerce Returns

Fixing things and building people – why we invested in Fixer

We recently announced our investment in Fixer, led by Founder Collective and including Chicago’s Impact Engine. Fixer is a service that fixes anything in your home reliably, on-time and at a fair price – founded by a contingent of Grubhub’s early employees, including Grubhub co-founder and long-time exec, Mike Evans. Fixer is also our first … Continue reading Fixing things and building people – why we invested in Fixer

Fixing things and building people – why we invested in Fixer

We recently announced our investment in Fixer, led by Founder Collective and including Chicago’s Impact Engine. Fixer is a service that fixes anything in your home reliably, on-time and at a fair price – founded by a contingent of Grubhub’s early employees, including Grubhub co-founder and long-time exec, Mike Evans. Fixer is also our first … Continue reading Fixing things and building people – why we invested in Fixer

How much do you want to sell for?

As our portfolio matures, I increasingly see the importance of the question “how much do you want to sell for?” From initial investment decision, to bringing on new follow-on capital partners, growing teams and ultimately exiting, this is a critical question for founders and investors to ask each other at each step to optimize ultimate … Continue reading How much do you want to sell for?

Four paths to entering B2B markets and clearing table stakes

As modal B2B software investors we frequently see entrepreneurs struggling with the drag of table stakes. How do you focus resources on an innovative or novel approach to the market when customers keep asking for table stakes? An example of this problem: Let’s say a company, Resu, is developing a software that reads knowledge worker … Continue reading Four paths to entering B2B markets and clearing table stakes

Flying for money: How to raise Series A and B outside Silicon Valley

Our strategy – serving our mission of great returns for our investors and entrepreneurs – is to assist our portfolio companies in raising a strong late Series A or B funding from a large fund, often (but not necessarily) coastal. Once through the gauntlet of finding product-market-fit, building out a team and finding repeatable sales, … Continue reading Flying for money: How to raise Series A and B outside Silicon Valley

Why I’m long the US economy (and millennials will buy cars and houses)

I’ve spent the last year scratching my head over the continued (and rapid) stock market rise amidst government uncertainty at home, geopolitical threats abroad and an increasing and ominous distance from our last recession. Large tax cuts for corporations certainly explain the recent run-up, but what of a near doubling over the last five years … Continue reading Why I’m long the US economy (and millennials will buy cars and houses)

Why I’m long the US economy (and millennials will buy cars and houses)

I’ve spent the last year scratching my head over the continued (and rapid) stock market rise amidst government uncertainty at home, geopolitical threats abroad and an increasing and ominous distance from our last recession. Large tax cuts for corporations certainly explain the recent run-up, but what of a near doubling over the last five years … Continue reading Why I’m long the US economy (and millennials will buy cars and houses)

Is your startup shock resistant?

A friend and I were discussing Chicago’s appointment of a Chief Resilience Officer, a role that focuses on the city’s ability to recover rapidly from economic, environmental or health shocks. This and Fred Wilson’s Worry post got me thinking about how shocks differ from other risks and how startups and investors digest and plan for … Continue reading Is your startup shock resistant?

Healing healthcare with startups

This is my first blog about healthcare and healthcare investing. When we started HPVP six years ago, we expected that 25 to 30% of our investing would be in healthcare IT. That didn’t happen because EMR adoption froze the market for the first four years of our existence. Every healthcare IT concept we saw had … Continue reading Healing healthcare with startups