The Journey Through Failed Experiments to Traction and Exit

I publish this series to discuss the nuances of bootstrapped entrepreneurship. Please subscribe to my Best of Bootstrapping series to never miss an article and?learn what to expect from 1Mby1M.

Entrepreneurs love to discuss success. Few are willing to discuss what they tried and failed at. When we spoke in 2019, Robly Co-founder Adam Robinson did a terrific job of sharing his journey through various failed experiments to a model that was gaining traction. Robly was bootstrapped to an 8-figure exit to private equity in 2021.

Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born, raised, and in what kind of background?

Adam Robinson: I was born and raised in Houston, Texas. I went to Rice University. I graduated in 2003. One of my friends had an internship at Goldman-Sachs the year before. I didn’t know anything about it, and somehow convinced people to give me a job as a derivatives trader at Lehman Brothers. For 10 years, I traded these real estate-related, credit default swaps. It was the most interesting job for someone in their 20’s. Everybody who was doing what I was doing was making a ton of money.

What was even more interesting was that the guys who started Vimeo and CollegeHumor started it in my apartment in New York. They tried to make a show like The Office about these guys.

My brother started a tech company too. It was really interesting being in this derivatives world. The apartment that we were living in was ridiculous. It was this big loft. It was an MTV crib type of place. I always had this fantasy of starting a tech company.

Then, the financial crisis happened. There were a couple of good years for the product that I was trading afterwards, but the government really clamped down with regulations. The market shrunk over a series of five years. I’m one of these people who believe that human beings need to be part of growth environments. To be in an environment that’s contracting is the opposite of that.

It was easy at that point to say, “I’m going to take however many years it takes and try to figure out how to become this tech entrepreneur and see what happens.” My approach was incredibly flawed. I had this mentor at Lehman Brothers who we all looked up to. As he was trading bonds, he had five or six very significant investments that he was involved in semi-actively.

That life, to me, seemed really interesting. It was so much more interesting than trading bonds. I was going to deploy half of this capital that I had saved up at five or six investments. I’ll find people to run them and that was going to work.

Wall Street has the tendency to breed overconfidence in life on people that do well because the value of the human being is measured by the perceived amount of wealth that you extract from the system.

Sramana Mitra: I think the other fallacy in the Wall Street way of thinking is, to make a lot of money in Wall Street, you have to move money from here to there. The human complexity is less present in Wall Street money-making machines.

Whereas if you have to build a business, you have to manage people, orchestrate, and navigate the human complexity far more than just moving money or everything being automated.

Adam Robinson: I couldn’t agree more. I couldn’t have had less experience in any of those stuff. I wrote a couple of big checks. My brother was doing a private equity round. In a healthcare thing, I invested a ton of money that went to zero over 10 years. I started a company with some other guys who also were totally inexperienced. They were in the staffing space.

Our conversation continues here.

Looking For Some Hands-On Advice?

For entrepreneurs who want to discuss their specific businesses with me, I’m very happy to assess your situation during my free online?1Mby1M Roundtables, held almost every week. You can also check out our free?Bootstrapping Course, our?Udemy courses,?YouTube channel,?podcast interviews?with VCs and Founders, and, to?follow my writings, click "Follow" from?here.