In my first company, I had built a polling application that was doing decently as a social website on college campuses and as a Facebook app.  We were working hard to think of new ways to acquire customers...classic B2C type stuff.  We had some connections to IBM and we started talking with them about how we could sell them on our platform.  Somewhere along the way, we thought that this app could be a great fit for enterprises as well.  Some kind of internal productivity app.  

Let me repeat that.  We were going to sell apps to IBM.

IBM toured me around the company with tons of conference calls.  I made proposals, calculated estimated costs, built mockups.  I worked my ass off.  I reached out to my advisors for help on the sales materials to make them perfect.  As money in my company was dwindling down, I stopped paying myself.  I was on the verge of closing a deal with IBM and optimistic that we would make it through.  We eventually did run out of money, so I funded the company a few more months on my own.

Finally, I pushed for a go/no-go meeting with IBM.  After months of talking and lots of excitement, my IBM contact said they were still interested by wouldn't have a budget for the product.  They said check back next fiscal year.

A sad ending to my little company.  We struggled another few weeks on our B2C strategy.  But we were done.  And it was my fault.

Not because I failed to close IBM.  I know now that we were never going to close IBM.  IBM doesn't do deals with startups.  They were happy to give an eager young entrepreneur a bit of their time, but they never had any intention of writing a check for our services. I should have never gone down that road at all.  Who knows if we would've been successful with our consumer apps, but I can say for sure that we would have had a better chance of success if we hadn't gotten so distracted with IBM.

Now, I know as an entrepreneur, I'm supposed to break down walls and do things that others don't think is possible.  But seriously, was this really the best use of our time?  I had no experience with enterprise software or B2B sales.  Our product wasn't even really a good fit.  AND IBM?!  With 20/20 hindsight, I can't think of a worse company to sell into.  They're big.  They're slow.  And wait for it...they're a fucking tech company!  Why would they ever need our help?

To be clear, this little strategic misstep was 100% my fault.  I pushed for it.  I was naive.  And I paid the price for my suckiness. 

But I got so much help along the way.  Advisers that proofed my proposals, answered my questions.  They mentored me.  They cared about me and wanted me to feel good.

This is hard to say, but I wish they had believed in me less.  Encouraged me less.  Supported me less.  I wish someone, anyone, had put a stop to my foolish ideas.  I'm incredibly confident and stubborn.  I believe I can do anything.  So additional support is kind of wasted on me.  What I really needed is someone that could break through my confidence and tell me straight that I was being an idiot.

It is possible to be this type of adviser.  I now ask better questions of my advisors and explicitly welcome their roughest criticisms.  I gravitate towards those advisers that rip into me with skepticism and challenging questions.  One of my oldest friends has been that adviser for years.  He never believes a word I say.  He pushes me to be better.  I love that.

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For the last couple of years, I've been volunteering for an organization called the Network for Teaching Entrepreneurship (NFTE).  Founded in 1987, NFTE brings business plan competitions into underserved high schools across the country.  Some families have parents that teach this stuff to their kids naturally through role modeling and at the dinner table.  Others rely on NFTE.  It's cool shit.

I noticed that there were always one or two students that wanted to take their idea further.  They had that itch that so many of us have spent our lives scratching.  They wanted to move beyond business plans and actually build something.  But they didn't know how.

Crystal was initially struggling to think of an idea.  Chris from Central.ly, helped her think through a dozen different product ideas until she landed on the TogetherPouch. Crystal is now making a group-snuggie that is targeted towards her own friends.  It's a totally unique blanket-pouch, in the shape of characters she creates.  By day 2, she had a prototype.  By day 3, she had a website and was set up to receive orders.  I would not be surprised to see TogetherPouch as the most popular Sweet Sixteen gift this year...

DeShawn came to NFTE with a love for making electronic music.  He had been selling his music as background music to indie artists and game makers, mostly in cash transactions to people he knows.  With a few days of hard work and missteps, the mentors helped DeShawn figure out how to set up a Weebly website with Soundcloud as a backend to host his music.  Now anyone, anywhere in the world, can purchase exclusive rights to Deshawn's original music.  Check it out.

Vivian is catering a magical Bubble Tea experience to startups in SF.  The mentors taught her Hustling 101.  Our new bizdev wizard, networked her way into getting Heroku to be her first customer (without our direct help!).  She's now working on a way to creat a shelf-stable version of Bubble Tea that she can sell in local stores.

When I was 19, I stepped on to Duke's campus as a freshman, ready to learn, party, and prepare for my career.  I met with my career advisor and planned a course load aimed at pre-med with a major in political science.  I figured I would either make it big in politics or become a doctor.  You know, one or the other.  Probably best to prepare for both by taking the right classes from day 1.  Not once did I ever think I'd become an entrepreneur.

Funny thing about entrepreneurs...we're not very good at following plans.

It was badass to make a bunch of money.  But by the spring time, I was back to lacking direction.  What was I going to do, leave Duke and become a loft maker?  Being an entrepreneur is not glamorous.  I didn't get flown out for in-person interviews like my consulting friends.  I didn't get a signing bonus.  Everyone kept asking what I planned to do after Duke.  I had no response. 

If you're 20 years old and unsure of what you'll do when you grow up...don't fret.  Welcome to the club.

I'm coming up on my 10 year undergrad reunion.  I'm not a doctor and I didn't go into politics.  I still have never received a signing bonus.  It's taken all 10 years, but I can finally tell my college buds what I plan to do when I grow up.  Damn it feels good.