Starting an Entrepreneurial Career – HOWTO

This post is based on a presentation I made to students in the CCEW Program at the University of Oklahoma about how to launch and develop and entrepreneurial career. Here’s that presentation, with a few extra notes. Enjoy!

1. Work with startups at all costs.

image32This is the most important thing you can do, if you want to launch an entrepreneurial career. It made all the difference for me.

You have several things going for you if you start early: You can work for cheap, startups are always looking for free and cheap labor, and you don’t necessarily need a high degree of skill or experience to have an impact.

Where to find startups? Check out your local meetup groups, tech talks or co-working center. You can work with student startups, but you’ll learn more working with startups that have raised at least one round of financing and have some additional structure and needs. Just ask around.

I started my entrepreneurial career working as a receptionist at a startup in downtown Houston. I ended up teaching myself application development while answering phones, published an app on the startup’s network that got write-ups in national industry magazines like PC Week, and ended up as their Product Manager for Internet Applications, until I found some investors and left to start my own company in London as founder and CEO.

2. Try stuff out. (Fail frequently and fast!)


This is the time to learn and fail and learn again, until you know what not to do.

Don’t be afraid to take risks and move on from failures quickly. Fortunately, we live in a society and a country where business failure is a fact of life and we have a culture of learning and renewal. Seriously. Hopefully you won’t encounter this too early, but you’ll find that our nation’s bankruptcy laws and general corporate law favor risk-taking and that many of the most successful entrepreneurs and business leaders have gone through many serious failures before reaching sustained success. And many of them have had to start over multiple times.

In my case, I was on my fourth startup before I hit my first home run. I got lucky. It could have been my sixth or eighth or twelfth startup. All success requires is a willingness to fall down and then get back up over and over.

As long as you’re totally honest, move quickly, willingly learn lessons and talk about them, you can bounce back from almost any business failure.

Obviously, be careful about using your resources and those of investors, but always remember that risk capital is meant to be risked! Do it!

3. Experiment. (There are no dumb questions.)


Do lots of different things!

This is similar to “Try stuff out” but goes further: Connect things together. Make strange associations. Push your boundaries and do things that you wouldn’t normally do. Ask difficult questions of yourself and everyone around you. Challenge conventionality. Challenge mediocrity. This is the only way progress gets made.

Experimentation is the favored method of building a startup business today, and there are many great tools and techniques to help with the process. Personally, I like the lean startup method, but there are many different approaches. Place many quick bets and watch what grows, and then follow it fearlessly.

4. Find people (mentors) who’ve done it before!


Find people who are willing to meet with you, informally, monthly, to talk about your experiments. Find people who are highly successful, but who also tout their own failures and love to talk about lessons learned. These are the people who will be interested in helping.

Where to find mentors? You’ll often find them in the same places that you’ll find startups, but sometimes, you have to go look them up and call or email them.

Focus on people who are successful in your local community, however you define that, and have an interest in helping the next generation. Don’t be afraid to write and ask people to help you. If you don’t ask, you won’t get. Grow a thick skin and learn to move on from rejections.

Keep in mind that you need to have something to offer. Don’t ask potential mentors if you can “have coffee and pick your brain.” People don’t like that. They have lots of demand on their valuable time.

Instead, think about what they might get in return for providing you with regular meetings and advice. Maybe they want early access to an investment opportunity. Maybe they want to grow their reputation in their industry, the startup community or the investment community. Consider adding them to your company’s advisory board. Give them free access to unique opportunities and resources.

Get creative and stay positive. Mentors love to work with relentless, energetic, passionate entrepreneurs.

5. Learn how deals work!


This is often the biggest deficit I run into when working with young entrepreneurs. They have a great idea, great talent and good execution skills, but they haven’t educated themselves about what a deal looks like and don’t understand how to step into the shoes of their counter-party to figure out how to create a successful partnership.

Whether they’re negotiating fundraising, acquisitions, joint ventures, partnerships or sales agreements, knowing dealcraft is critically important!

This is one skill that you can’t afford to learn exclusively by doing. There are some good books on this. Read them. There are also great startup lawyers who will effectively provide you with an deal-maker’s MBA, if you’ll read every document more closely than they do and ask lots of questions. Working at a startup and insisting that being in-the-know about the company’s deals is the price the company pays for your deeply discounted labor, is another good route.

Not knowing about how deals work – terms, negotiations, personality dynamics and deal tempo – is the most costly mistake that early-career entrepreneurs make. Avoid it!

6. Show up! Go to events. Meet people.


You want to get ahead in an entrepreneurial career? Show up! There’s no way to get ahead in an entrepreneurial career without meeting a lot of people. And, keeping up with them. Fortunately, there are a wealth of tools available to make that happen, but you have to use them. Carry lots of business cards. Old fashioned, but they serve the important purpose of getting you onto somebody’s LinkedIn list.

Knowing a lot of people is a huge advantage as an entrepreneur. Once you build up a sizable network, you suddenly have an inalienable resource and deep pool of available knowledge, experience and connections. It is surprising how many times knowing the right people has made all the difference in my life-long entrepreneurial career.

Where to meet people? Go to events. Most major cities have a good central calendar. In Oklahoma, there’s our directory, StartupOK, which includes a plethora of event organizations and links to up-to-date community calendars. Find something similar in your community!

If you’re in Oklahoma, here are few ideas to get you started. (You can do more research on StartupOK): OpenBeta, TEDx Events, Pitch Days, 1M Cups, Startup Weekend, InnoTech, OKBio, Oklahoma Venture Forum, Thunder Plains, User Group Meetings, Inspire Conference, Confluence, SoMoLo

7. Read like crazy! (Learn from others’ mistakes.)


Mentors are great, but there are only so many meetings they can take, questions they can answer and coffees you can drink. When you start your first company, you need a lot more knowledge, fast!

You know the drill. Grab your tablet and download some great business books! There are lots of guides to what to read when it comes to valuable business and entrepreneurial books:

25 books that every entrepreneur should read

33 business books every professional should read before turning 30

37 Books That Will Make You Better at Business

In addition, keep up with the latest news and analysis by regularly reading the top startup news sites and blogs out there. Here are some of my favorites. They’re amazingly cool, surprisingly free, and often hilariously snarky:


So, here’s how you do it, one step at a time:

  1. Work with startups – at all costs!
  2. Try stuff out. (Fail frequently and fast!)
  3. Experiment. (There are no dumb questions.)
  4. Find people (mentors) who’ve done it before!
  5. Learn how deals work!
  6. Show up! Go to events. Meet people.
  7. Read like crazy! (Learn from others’ mistakes)

Starting an entrepreneurial career is one of the best moves you can make with your life. There’s just no comparison. (60 Reasons Why Entrepreneurship Is Amazing). Start early, do it the right way, take chances and have a good time. You won’t be sorry!

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This blog is dedicated to providing advice, tools and encouragement from one entrepreneur to another. I want to keep this practical and accessible for the new entrepreneur while also providing enough sophistication and depth to prove useful to the successful serial entrepreneur. My target rests somewhere between the garage and the board room, where the work gets done and the hockey stick emerges.