Paving the Way for Future Entrepreneurs and Ten Tips to Make it as One

For over 20 years, I have lived a dual life. Don’t worry; it’s nothing shady or illegal. I have simply managed to strike a balance across two highly complementary careers:

  • Serial advanced tech entrepreneur and CXO
  • Professor of Entrepreneurship & Innovation

On the entrepreneurial side, I have been CXO of eight successful VC-backed enterprise tech startups, hiring scores of product marketers, product managers, business development executives, growth hackers, content developers and social media strategists.

On the educator side, I have been a senior lecturer at MIT and the Technical University of Denmark for over a decade, and am currently Global Professor of Marketing, Innovation & Entrepreneurship at Hult. In addition, I have judged MIT’s $100K entrepreneurship competition for over a decade, as well as having judged and mentored many top startup accelerators including Tech Stars, Y Combinator and BetaSpring.

How are these roles complementary? Being a practicing entrepreneur keeps me hyper-current, as the field evolves so rapidly and dramatically. This ensures that what I teach and how I mentor remains relevant and actionable to the next generation of aspiring entrepreneurs. Likewise, I am able to hire some of my very best students, helping them realize their dreams while my startup benefits from their invaluable contributions.

As a result, I have had the opportunity and, more importantly, the privilege to help pave the way for thousands of young entrepreneurship students and hundreds of entrepreneurs from around the world as I balance my careers as professor and entrepreneur. I consider myself incredibly lucky to have worked to this role. In many ways, I consider it my life’s work.

Entrepreneurship is not as Glamorous as Hollywood Potrays

Entrepreneurship is the equivalent of running a marathon at the speed of the 100 yard dash with high hurdles everywhere along the track. To call it challenging is an understatement of epic proportions. For every gushing article celebrating the successes of the next generation of entrepreneurs, those few companies who successfully raise money on Shark Tank, or even the endless stream of coverage documenting the breathtaking success of the chosen few (Google, Netflix, Uber, Airbnb, WhatsApp, Snapchat and Dropbox), there are countless other companies that never achieve lift-off despite heroic efforts, or that crash and burn after early success. For every Facebook, there are ten thousand failures.

It is not Solely about Smarts or Work Ethic

I have had many bright students and mentees that would never make it in a startup. This is not a testament to their intellect and will to work hard. In some cases, I have successfully coached them toward career choices more appropriate to their skill set and personality. In others, I attempted to coach them away from it, only to have them decide to try it anyway. Inevitably, most of them failed. Some failed two or even three times before finally realizing that entrepreneurship was not for them.

Yes, the odds of failure in a startup are well-documented. There are far easier ways to make money. Being an entrepreneur is one of the hardest things you’ll ever do. You have to be comfortable with ambiguity and “failing forward.” You regard failure as an event, not a reflection of your character. You have to be confident in your ability to come up with quick hacks to circumvent inevitable obstacles in your path and to be a “pragmatic optimist” with an “impossible is nothing” mindset. Effectively managing the daily emotional roller-coaster is an inherent part of the experience, requiring a high level of self-awareness. No one chooses this path to get rich quickly. You do so because you cannot imagine not doing it. I believe that entrepreneurship is a “calling” – not simply a career choice and certainly not a job. After many years, I have developed the ability to quickly assess which of my students and mentees take this to heart, conveying a “fire in the belly” intensity & attitude. These are the ones that I am especially drawn to pushing toward a career in entrepreneurship.

10 Suggestions for those committed to the entrepreneurship journey

1. Learn from those doing it now. Take an entrepreneurship course with current entrepreneurs- not someone who did it ten years ago or a purely academic professor with no concrete experience. Keep it real and learn from their experiences.

2. Reach out to seasoned entrepreneurs, like your professors, for a heart-to-heart about what’s real and what’s not in this unique ecosystem. Share your ideas and get constructive feedback on how and where to best enter the ecosystem given your interests and skills.

3. Seek out other like-minded people. Join a Meetup group in your community focused on startups and discuss with them their passions and work.

4. Attend a Demo Day – the ninety-day “graduation” event for top tier startup accelerators in a city near you. This could include Techstars, which has “mentor capital” programs in cities across the globe, or make the pilgrimage to Y Combinator, the place where unicorns like Airbnb and Dropbox got their start, and whose base of operations is in Silicon Valley.

5. Participate in Hackathons to determine if you are comfortable working under intense pressure with a small team of people to solve hard problems. It serves as a great approximation of the pace and intensity of startups, and typically lasts from 12 to 72 hours.

6. Enter a startup business plan competition at your school or in your community, testing out your ideas with those around you.

7. Aim to get an internship at a startup, be it paid or unpaid. It could be a great window into the lifestyle. Seek out supervisors who will make time to mentor and lead you through the environment.

If you want to start your own company, the bar is even higher. In addition to the above suggestions:

8. Read Noam Wasserman’s essential book “Founders Dilemmas” for invaluable insights on founding and leading your own company.

9. Entrepreneurship is a team sport. Network your tail off to find appropriate co- founders. Follow the Founders Dilemma book’s advice rigorously.

10. Enlist a few, select mentors/advisors, who can provide guidance and also connect you with top startup lawyers, accounting firms, etc.

And, one bonus piece of advice:

11. Be coachable! Ask for advice and take it to heart.

While I could never guarantee that this advice will make you successful, I am confident that if you take it seriously, it will certainly improve your odds of success. Why? It has worked for me as I have been on both sides of the court as professor and entrepreneur and it has worked for many of my mentees.


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