5 advices from the guy Elon Musk wants to be when he grows up

Igor IZotov
4 min readMay 15, 2019


Before coming to Chicago I had three people on my mind. Al Capone, the first real Chicago entrepreneur who is unfortunately long dead ;) , Richard Thaler , the father of behaviour economics — still has not replied to any of my emails and Brad Keywell. For those who don’t know who Brad is, think about the guy who founders Groupon or Uptake, the hottest startup in the states for three years in a row, beating slack or uber to the tittle. This guy founded 9 companies out of which 3 are publicly traded on the NYSE, where he still holds the record as the youngest CEO of a publicly traded company, something he accomplished at the age of 28.

Yap still feel uncomfortable to ask a person to take a picture of him

And guess what, this morning I had breakfast with him, or better he let us, fellows of the US State Department pick his brain for an hour. Slave to rationality and slave to opportunity, at first glance Brad looks like a quit person, but as his brain wakes up, he because this inspirational hero of almost 8000 people that work in many of his companies, under one roof in the formal printing houses of the Chicago Tribune.

For him America is the greatest nation of the world for one reason — the bankruptcy laws which helped him become what he is today, multiple times. It didn’t help him in a way to trick his shareholders (as one US president did) but taught him about failure and what it means to think creatively. By the age of 28 he was worth 60 mil $ in shares, by the age of 30 he was broke with 2 children to feed. As he found out money are NOT the answer, just the opposite, not having them is a blessing in disguise, as it gives you the opportunity to find out how failure looks. When you hit rock bottom it’s only then you are doing things more creatively. Thus, his first advice — FIND AND DO STUFF WITH PEOPLE WHO HAVE FAILED.

From early childhood he was a weirdo, starting business where others saw pot and beer (there goes the debate if entrepreneurs are born or raised ). He never told his parents what he was working on as he says parent are bad source of positive feedback. Instead he makes mental models how the world works and writes down the skills that are needed to make shit happen. And thus the second advice to all entrepreneurs out there — THERE ARE INEFFICIENCIES IN THE WORLD AND the role of the entrepreneur is to find them and make money out of them. The entrepreneur is the equivalent of the arbitrage stock trader who scrappers the stock exchanges, to find the mispriced stocks. There is no shame on coping and improving something that already exists and Rocket Internet in Berlin is a great example of company that made millions of dollars by copying US startups and bringing their ideas to the European continent (Zalando = Zaposs);

As the breakfast moves on I realise that this man runs and starts more companies that I have friends and the logical question is how is he managing it all. But how does he do it? Beside being mentally super-strong, has a whole army of psychologists, yoga and meditation specialists, Brad work one company at a time. He doesn’t move to another company till the moment he is sure that the management team is capable of leading the company. For example in Uptake he knows where they will be in 5 years. As a leader of people he knows his daily job is not to work on the mental happiness and bla bla of his employees or shareholders but his only job is to OPTIMISE THE REWARD AND MINIMISE THE RISK.

Even though, by 2024, 3 out of 4 business started today in the US will not exist anymore and Brad still decides to invest his own money into startups. I mean when you are the founder of Groupon, the company that energized Chicago’s tech scene, what do you do with the rest of your life? You stay in Chicago and start more unicorn companies, InnerWorkings, a tech-based marketing firm, and Echo Global Logistics, a transportation brokerage firm. Fund others with a VC firm with your own money — Lightbeam, and get involved in Chicago’s civic and philanthropic community though Future Founders as chairman of the board, i wrote about them already, and Chicago Idea — founder, one of the largest innovation and ideas gatherings in the world.

So the logical conclusion to this text and our breakfast was, what are you looking for in the 250 or more startups that you look at every year?

his only question is and always will be Why MUST YOU EXCIST — the fourth and most important advice that he had for all of us.

Every week Brad sends email with his personal thought to his employees and every year they make a book out of them

Wanna know more check izotovconsulting.co



Igor IZotov

W.R.I.T.E.R - "Not particularly intelligent, but passionately curious by nature"; FYI I make typos all the time