The best advice I’ve ever gotten

And the cathartic story behind it.

There comes a time when you need to call it quits, whether you want to or not. I was there recently and it was gut-wrenching. My most ambitious startup yet, Trove, failed after five years of blood, sweat, tears and too much money lost. Further, my whole life needed to be re-evaluated, fast. I was on a dangerous path to losing my family and possibly my life. This is that story.

Like many, it begins wide-eyed and positive. Basically, I like to try things. I am OK with risk. I believe a good team can solve almost any problem and enjoy doing it. I like building something from the ground up. I get a lot of satisfaction from people using what I help create. These traits have inspired me to start several companies over the years.

Trove was to be a culmination of my life’s work so far. For a decade, my co-founders and I had worked with data and communications. We built some of the first anti-Spam and data de-duplication technology. Years before AWS, we created a petabyte-scale cloud storage network. After Barracuda’s acquisition, our product became the #1 selling backup appliance. At Trove, we were excited to apply cutting edge AI to email. We expected to easily identify valuable services once we could interpret email in compelling ways. After all, if companies will spend lots of money protecting it, they’d surely pay to put it to better use, right? We raised over 13 million dollars from incredible investors and created some astonishing technology, but we did not find a worthwhile product-market-fit.

Unfortunately, I had also failed to take a critical lesson to heart. Don’t try to do too much at once. Instead, focus on doing a few things, ideally one, really well. My appetite for trying things resulted in too many things going poorly. Trove was one of them and it did not survive. That’s when I got some solid advice from good friends and my wife. They told me to focus on cleaning it all up. They encouraged me to make this one thing my primary job, before tackling anything new. Just last night, I was reminded of this basic principle yet again. Talking with Philip Shane about the value of recognizing your constraints, Rand Miller, the co-creator of Myst, espoused how fulfilling doing a small thing well can be.

A few weeks before I received this critical advice, I was discussing the future at Zingerman’s Roadhouse with Trove’s final sixteen people over breakfast. We had survived a difficult reduction in force and were ready to execute an ambitious pivot. Then, a week later, our funding plans fell apart and Trove was finished. My co-founders and I imagined hiring everyone into a new startup and carrying on immediately. We were determined to keep this group together. We made arrangements to put everything we had left behind it, creating about six months of new runway. With no product, no customers, no revenue, and no investors, this plan boiled down to repeating our past mistakes, only worse. Thankfully, we followed the clean up advice instead.

All there was to clean up

To understand the extent to which my life needed to be “cleaned up,” it’s helpful to travel a few years back in time. That is when my personal stress peaked. My family has a history of heart disease. Looking back now, I know my stress level was unsustainable. It could have easily been the death of me. What I learned is mental stress carries cumulative effects similar to environmental impacts. Each individual decision to take on one more thing was fine by itself, and seemingly worth the effort and risk. However, as the range of these things all inevitably yielded their own set of challenges over time, the stress compounded and became too big to deal with effectively. In other words, it all built up quietly and slowly, from thousands of small choices pushing until the dam broke. Here is a quick rundown of what was on my mind at the time…

All together, my companies were burning through over a million dollars per month at one point, with little to show for it. Trove had no revenue or product market fit and Nutshell, despite spending a lot of new investment dollars, wasn’t growing faster. Personally, my life savings were consumed by Cahoots, a real estate passion project to build a Tech Hub in Ann Arbor that was millions of dollars over budget and fraught by seemingly endless construction issues. We fired the two companies contributing to those problems, leading to a series of lawsuits that also demanded attention. I was managing dozens of subcontractors directly and needed to find a new construction manager.

At home, I was focused on my son, Asher, who has developmental Dyslexia and needed early literacy intervention. His school had mismanaged its Child Find responsibilities, limiting the services he received and putting us into a legal conflict with Ann Arbor Public Schools. The year was capped off with a relationship crisis with my wife that threatened to end our marriage. Sometimes, I would lay in bed and try to list out the major things I was stressed about on each finger. It would sound something like this,“Trove product strategy, Trove funding, Nutshell burn rate, Cahoots lawsuit, the other Cahoots lawsuit, Cahoots construction, Cahoots finances, Asher’s IEP (Individualized Education Plan) process, my daughter Zoe’s Apraxia intervention, my marriage, I know I’m forgetting something.” I know nothing can ever compete with 2020 but I really didn’t love these few years either.

2017-2018 timeline — When things were going from bad to worse:

• Escalating legal fight with original Cahoots architect.
• Original Cahoots construction co. terminated, leading to a real estate lien and more litigation.
• Trove and Nutshell both burning too much investment money.
• Conflict over child find emerges with Ann Arbor Public Schools.
• Marriage relationship reaches crisis.

The right place to start

This was a lot to take on, but also, mostly things I had created myself. I did not want to give in to feeling overwhelmed. I knew the stress would begin to reduce as I made good choices. Most importantly, everyone in my life was physically healthy. As far as hardships go, mine deserved little sympathy in comparison. I decided to start with my marriage. It’s important to note this was, regrettably, a first for me. It was not a purely conscious choice but I had consistently put my work life above my family life. I made a commitment to Robin, my wife and partner of over fifteen years, that anytime work needed to be sacrificed in service of getting our home life and our relationship back on track, that’s what I would do. She deserved to have her needs put above my pursuits. I’m eternally grateful to her for sticking with me and the opportunity we’ve shared to recommit to and improve our life together.

Finding common ground

I cried. I don’t do that often, but there I was standing by Robin in the bathroom getting ready for an art center fundraising dinner, crying. They were big, unexpected tears. It just hit me. Earlier that day I had told the remnants of the Trove team there would be no ability to go forward together, as we’d hoped. It marked a final acceptance of reality and an emotional release years-in-the-making. I wouldn’t call it “relief” exactly but there was an undeniable emotional power in letting go. For years, I had been determined to plow through all obstacles. Delivering a successful outcome for this group was deeply important to me. I didn’t realize how much weight I was carrying around and now that it was gone, it came out spectacularly.

Getting things under control would be a lot of work. I needed to know who I could work with to do it. To start off, I met with my co-founders Lindsay and Ian. We discussed each other’s future plans and the work ahead to do. The three of us have worked together for two decades. We are closer to being family to each other than colleagues. I told them I would support whatever they want to do next, whether together or apart. We agreed to focus our energy on fixing things together and go from there.

My other relationships needed to be considered at this time too. I must say a special thanks to Andy Jensen. He voluntarily stuck around for weeks completing countless Trove wind-down tasks, which helped in more ways than he can know. Some of my relationships had been unintentionally neglected. These required reconciliation and a renewed investment. Others had been distracting, or worse, for too long and I had to move on. I faced each situation honestly and transparently. I admitted my mistakes, accepted reality, blamed nobody else for failures, asked for help, and acted decisively. These conversations were hard but they were necessary and rewarding.

One step at a time to solid ground

There is nothing quick about picking up the pieces. If you are coming off of a big failure, here’s my advice — Be patient and take your time. This is not what we entrepreneurs like to hear. We are bent towards big disruptive action. Shortly after Trove failed, Peter Wilkins told me:

“You’ll feel like your arm as been chopped off and you just want to replace it and move forward, but you can’t. You need to go through the process and learn from it.”

He was right. My healing process began over a year and a half ago now. That was when I realized how bad things were. I have been methodically trying to make one good choice after another ever since. And, that plan is working.

2019 timeline — Focusing on “cleaning it all up.”

• Dispute with original Cahoots construction co. settled after 10 months.
• Dispute with original architect ended after 33 months at case evaluation by accepting a financial benefit awarded to Cahoots.
• Trove financing plan falls apart and company fails.
• Conflict with Ann Arbor Public Schools settled at mediation.
• Cahoots finishes construction and fully opens!

Solid ground

Not many people would look at 2020 as a year of “solid ground” in their life. For that, I feel tremendously blessed and grateful. Hard work does pay off. Despite Cahoots closing temporarily during the COVID shutdown and the uncertainty surrounding every business right now, including Nutshell, things are good overall. Cahoots recently completed a mortgage refinance with our friends at the Bank of Ann Arbor, which provides some financial stability during the continuing Coronavirus crisis. Nutshell has its eye on the future with an ambitious Growth Software vision. As far as Trove goes, I’ve dutifully checked every box I can think of on what a founder should do in this situation. For months, I wore a “Fiduciary Responsibility” hat and essentially worked for Silicon Valley Bank (our primary lender) until the assets were handled in the most responsible way possible.

2020 timeline — Finding “solid ground” during a global pandemic:

• Cahoots temporarily shutdown by COVID and completes a mortgage refinance, creating financial stability.
• Nutshell focuses on the future with its Growth Software vision.
• Cahoots reopens with COVID-19 safety measures in place.
• We start a new company.

The next act

What a difference a year makes! I’m now fully in the mode of transitioning from cleaning things up to starting something new again, and I’m loving it.

After a year spent considering our options carefully, we’ve found something I’m excited to work on. It combines our technical experience from Trove with a clear and present market need around remote working. On a personal note, I will be able to evangelize the philosophy of doing a few things well and explore how technology can aid in this practice.

I promise details on the new thing will come, but for now it was important for me to write a little about this experience so I can truly move forward and past it all. For anyone who finds themselves in a difficult time, I hope you can step back and find similar support in your life to set things right!

P.S. — Thank you to Robin, my loving wife and partner for life.