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Best of Bootstrapping: Discussing the Journey Through Failure to Success

Posted on Friday, Nov 15th 2019

Entrepreneurs love to discuss success. Few are willing to discuss what they tried and failed at. Robly CEO Adam Robinson does a terrific job of sharing his journey through various failed experiments to a model that is now gaining traction.

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’s 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.

This segment is a part in the series : Best of Bootstrapping


. Bootstrapping to an Exit
. Why is Bootstrapping Important?
. How Can You Play this Low-Probability Game Intelligently?
. Do NOT Go to VCs as Beggars - Go as Kings
. Excess is NOT Required for Success
. Bootstrap First and Raise Money Later
. Some Bootstrapping to Exit Case Studies
. The Buy Side of Bootstrapping to an Exit
. Blitzscaling vs. Bootstrapping
. Bootstrapping to Unicorns
. Cinedigm Acquires Bootstrapped 1Mby1M Company Future Today for $60 Million
. Mailchimp Bootstraps to $600M Revenue
. Bootstrapping from Arizona to $10 Million
. Bootstrapped Basecamp Executes a No Nonsense Strategy
. How Under30Experiences Bootstrapped to $5 Million
. Bootstrapping with a Paycheck
. How Algo.ai CEO Amjad Hussain Bootstrapped using Services from Michigan
. Seed Investors Who Like Bootstrapped Businesses
. How iHeartRaves CEO Bootstrapped a Niche e-Commerce Company to $20 Million
. Bootstrapping with Services
. How The Intern Group CEO David Lloyd Bootstrapped to $13 Million
. How Passageways CEO Paroon Chadha Bootstrapped from Indiana
. How SmartBuyGlasses CEO David Menning Bootstrapped to $50 Million
. Death by Overfunding
. How RainmakerForce CEO Mack Sundaram Bootstrapped Decisively to $5 Million+
. How FormAssembly CEO Bootstrapped a Virtual Company with a Paycheck
. TimeSlips CEO Mitch Russo Bootstrapped to Exit with Sage
. The VC-Entrepreneur Compensation Disbalance
. BioConnect CEO Bootstraps with Sophisticated Strategic Maneuvering
. Tremend CEO Marius Hanganu Bootstraps from Romania
. Gesture CEO Jim Alvarez Bootstraps to $10 Million
. SproutLoud CEO Bootstraps to $30 Million from Florida
. Tuft & Needle CEO Bootstraps to Over $100 Million
. Co-founders Bootstrap Linguamatics to Over $10M from the UK
. Ownership Matters
. Vainu Co-founder Mikko Honkanen Bootstraps from Finland
. Entrepreneur Couple Bootstraps to $10M from Colorado
. Power2Motivate CEO Bootstraps to $80M from Canada
. Financial DNA CEO Bootstraps to $10M+ from Australia
. Big Barker CEO Bootstraps a Niche E-commerce Brand
. PrecisionLender CEO Bootstraps to Over $10M from North Carolina
. Master Bootstrappers with Over $1B in Exits
. Ultra Mobile Founder Bootstraps to Over $100 Million
. Bootstrapping a Two-Sided Marketplace to $10M
. Can You Bootstrap a Virtual Company to Over $5 Million?
. Capital Efficient Entrepreneurs Turn $1M into $80M
. Discussing the Journey Through Failure to Success
. From a Small Town to $12 Million
. Bootstrapping to Y Combinator and $10 Million Series A
. Bootstrapping a Marketplace to Over $10 Million

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