4 Important Lessons I Learned From Jumping into Entrepreneurship Head-On


A lot of people start feeling super-awkward about themselves when they contemplate starting their own business…y’know, a tingley-feeling of “should I really be doing this?”  ”Will I uber-fail and people will think I’m an idiot?”

I worried about all of those things…but decided “to hell with it, YOLO!”, and gave up the idea of pursuing a “normal” career; opting to jump head-first into entrepreneurship after I graduated from college.

(I promise I don’t say YOLO in real life).

And I sit here 10 months later…reflecting back to all of the things I’ve done…

…some of them have been ingenious…

…most of them have been downright stupid, and can only be chalked up to a “learning experience”

So I decided to take my experiences…the good, the bad, and the shitty…and distill them into this super-long, heart-spilling missive.

TLDR??..if you’re serious about starting on your own, and don’t want to spend months making mistakes, take this opportunity to learn from my mistakes, and do better yourself:

1. Start with a business where you are in control.

Super Nintendo Controller

A couple months back, I wrote about the striking value of a foundational business for first-time entrepreneurs; that is, a business that’s entirely within your control to execute (and therefore, a business that you’re not waiting around for others to chip in and do their parts for in order to be successful).

The point of this article was to specifically counter the popular notion of “bootstrapping a risky tech startup with a group of pals / some random guy you found on Craigslist”.  That is, “if I can just come up with a great idea and put together a ragtag group of guys to help me”, success will be right around the corner.

Look, you can be successful that way (it has happened).  But there’s a problem:

It’s well-known that top entrepreneurial incubators (like Y Combinator) make decisions based on the people in the team more-so than the idea, and that one of the top sinkers of early-stage companies is personnel / partner issues.

My experience and observations show that an egalitarian group of people who come together for the purpose of doing a startup who have no skin in the game and no clear indicator of leadership are especially doomed to failure.

Ye, good sir, hath trideth my patience!

Ye, good sir, hath trideth my patience!

What if your programmer gets tired of you, and just wants to leave?  What if your partner’s cash runway runs out before yours does, and they have to go back and get a fulltime job?  What if your partners get hooked on to some other venture, and leave you in the dust?

If you can’t make anyone stick around and you’re powerless to guide your company and your vision, how do you expect to achieve success?

It’s pretty easy to see why startups that start like this often fail.  Think of all of the things that have to “just happen” to line up between you and your cofounder (call it the “mojo” or “chemistry”):

  • Cofounder is as passionate about your idea as you are
  • Cofounder has the same “runway” as you, and can afford to devote the immense amount of time needed to launch a startup.
  • Cofounder is someone you just happen to get along with perfectly.
  • Cofounder is loyal to you in the long term.
  • Cofounder has exactly the skills needed to add value to the business.
  • Cofounder has to be willing to make this startup a central focus of their lives, just like you have.
  • Cofounder has to ….etc.

So, you are not only wasting your time by waiting around for a perfect person like this to “just come along” (like Rapunzel up in her tower)…you’re also just gambling that the person you do eventually wind up working with is going to be “perfect” enough to stick with it long enough to make this work with you.

Imagine a different situation:

What if everyone invested $10,000 into the venture and would lose their investment if they decide to quit?  What if you were paying the programmers, and they would lose a stream of income if they decided to leave your startup?  What if you were somehow ensconced–in a tangible, specific way–as the leader of your company, and had your partners’ unwavering loyalty?


“But I don’t have money to afford this, or enough experience to feel comfortable doing it.”

I know!

That’s exactly why you should start with a foundational business.

Before I started doing startups, I totally drank the “tech startup” Kool-Aid.

I thought, “if I can just go find programmers to help me, I’ll be able to launch a tech startup; no problem.”

And you know what the cool thing was?

found programmers!  5 of them, to be specific, through a local university as part of a for-credit class.

As grateful as I was to have the chance of bringing my venture to life, the problems with this model quickly became clear:

  1. The programmers were responsive to their syllabus and professor, not really to me.  That meant that they were gonna work at 1 speed, and there wasn’t much I could do to help.  That means that pivots are difficult, the design cycle has been long, 
  2. Programmers not as technically-inclined as would have been optimal.  Don’t get me wrong, they’re a talented group; but they are learning as they go (as opposed to someone who had 3 to 5 years of experience).
  3. A lack of “passion”.  After all, they are programming this as part of a required class and aren’t really being paid…why would they be super-passionate about it?

Now compare this to if I had been able to afford to pay / hire a programmer to help me out.  I could have hired someone with that 3 to 5 years’ of experience, and have them be more responsive to my needs and the feedback I got from users.

Don’t get me wrong: I’m not complaining, and I’m super grateful for my programming team and their work.  I’m simply pointing out that I gave up an immense degree of control by going down that route, and in many respects put my propensity for success into the hands of another.

If I had juts spent that time developing a foundational business at first, I could have raised the money to hire talent, and have raised my stature as a business leader within the community.

2. Hustling is probably the most valuable thing you can spend your time on.

Do the hustle!

Do the hustle!

One of the most striking correlations I have seen in my entrepreurial ventures is the disproportionate results provided by hustling; that is, actively going out and seeking valuable business connections.

For example, this blog.  Hustling has gotten me over 250 subscribers in the first 6 months, and relationships with other big bloggers (compare that with my old blog that got 50 subscribers after 6 months).  I spent immense amounts of time writing guest posts and making connections with other bloggers.

I’ve started a web development company (more info on that coming later), and the results I have gotten there from hustling have been immense: simply going to networking events, trying to befriend people and building relationships has worked wonders.  It’s been rather easy to excel above and beyond the usual “sleazy web developer” stereotype because we went out and hustled for business.

I’ve hustled mainly in 2 ways, both of which have had immense payoffs in the last few months:

3. Great mentors are worth their weight in gold.

An article by Penelope Trunk pointed out that one of the biggest factors in determining an individual’s career success is the quality of their mentors that they had by the time they turned 25.  (I regret that I can’t find this article, but it’s in there, and Penelope writes extensively about mentorship; you should definitiely check it out).

And I rather impolitely pointed out in a previous article that you are dumb if you don’t have mentors (but I also pointed out some tips on how to get kickass mentors).

Before I started doing startups, I was petrified to go up and talk to people.  See, I had this “thing”…where I thought others would look down on me because of my lack of knowledge.  That made it tough for me to go ask others for advice.

Eventually, I just started making so many stupid mistakes with my startup stuff (and getting frustrated & angry) that I knew my only option was to seek out the help of others.

And after I got over my sense of fear of being wrong (and my hubris of thinking I had it all figured out), I got on the track pretty quickly (I found mentors at a local university to help me make startup connections that could help with Focosos).

4. Over-planning is stupid and is used as a crutch by those who are too afraid to take action.  Take action first, and then plan second.

No point in overplanning...get out there and do something.

No point in overplanning…get out there and do something.

When I decided to start my web business, I decided to do something different than what I had done with Focosos.

With Focosos, I sat aruond and planned all day long.  I wrote a business plan.  I tried to predict all of the questions people would ask me, and what I would answer.  I tried to think about the “best strategy” for getting programmers to help me program it.

Days turned into weeks.  Weeks turned into months.  Progress was made, but it was slow and frustrating.

With my web development business, I spent, at most, 10 hours “planning”.  Then I hopped into action.

I cold-walked into stores on Main Street and asked if they needed websites (I’ve actually gotten 2 clients doing this).  I asked them “what’s been your experience with websites?”, and I learned about how many of them had been burned by shady graphic designers and web developers in the past.  I learned how many of them were actually super-excited by the prospect of getting a website, but simply had no idea where to start and what to do.

Through talking with prospects and slowly picking up new clients, I figured out how to market my services optimally (focusing more on “web branding and marketing” instead of “web development”, because branding and marketing is a more comprehensive service offering that more directly offers a specific ROI, as opposed to just making cute websites).  I figured out how to stand out from the crowd of sleazy, shady web development companies that had burned the trust of so many of my clients in the past.

I made great friends with some spectacular business owners (insurance agents, sellers of surplus military equipment, photographers, art gallery owners, and more), and learned more about their businesses and how I could provide value to them.

But would any of this had happened if I had just sat at my desk, trying to “strategize” how to make business connections?

Of course not.

I knew that by going out and trying to make something happen, I would be able to very quickly see what did (and didn’t) work for pitching my services to other business owners.

Now, when I do go to write my business plan, I can approach it more from a sense of “this is what I know people want”, “this is the value I can offer”, “this is how much money I can make”, “this is how long it will take”, and most importantly, “this is what the long-term payoff is.”

So get out there, learn the hard way, and make it happen.

Next week, I will write about some big shifts coming up in my business (one of them has already been immensely profitable, and I’m excited to share it soon).



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