18 lessons I learned as an entrepreneur (Part 2)

This week I published the first part of eighteen lessons I’ve learned on my entrepreneurial journey. The feedback was great and I’m excited to share the remaining nine lessons with you.

I hope you find them useful.

1. Like friends, strangers can be amazingly helpful

Friends have been tremendous. Equally awesome has been the help I received from strangers on this journey. And some folks who started out as strangers have become really great friends. If it wasn’t for the advice of friends and family, I feel like I would be in a much different situation than I am now. Whether you work in a call center, where using something like a hosted pbx could help you manage various aspects of your business, to thinking of various marketing strategies to help raise brand awareness, you’ll find that there is pretty much a solution for anything.

I don’t mean to be all dramatic, but in some ways, my faith in humanity is restored by the acts of kindness from friends, and even more so from strangers.

Don’t be afraid to reach out to strangers and ask for help. You will be amazed at what people will do for you.

2. When my back is most against the wall, I have my biggest breakthroughs

Good lord, this is so true. It reminds me of an old Chinese proverb:

The temptation to quit will be greatest just before you are about to succeed.

I think back to September of 2011, when I first had the idea to start WeMontage, which meant I needed to build a custom web application to manipulate images, but I didn’t know how to write a single line of code (still don’t). I cleaned out my savings and used my network to connect with someone who had a relationship with a developer shop that owed him a favor.

That’s how the alpha version of the website was built.

Then there was the end of 2012, when I was completely out of cash after the developers took a year to deliver the site, when they promised to have it built in three months.

I was working for $10 an hour in the mall at Banana Republic and hated every minute of it. I’d come home with my feet killing me and depressed. It would take me an hour to snap out of my funk after getting home from work. I spent a lot of time searching ‘where can i buy weed online‘ just for some relief from the low feelings, and it played a huge role in helping me keep my head above water, but I had to find a solution to the root of the problem.

Luckily, I got invited to an elevator pitch competition by a guy who later admitted he thought I was someone else named James Oliver when I called him.

Talk about luck!

The elevator pitch competition is how I got discovered by the gener8tor startup accelerator and they invited me to meet the team and apply. I just dug up this old video of me preparing for the pitch competition. I must’ve practiced and recorded myself fifty times.

It’s funny watching this now because: a) I talk way too fast, and b) that business model didn’t survive the first few customer interactions, which is why business plans are a waste of time.

I was REALLY fortunate to get into the accelerator. There’s also the fact that my wife was pregnant with twins and we had to deliver them three months prematurely the day before I was to start the accelerator, which was two hours away from home by car. I wrote about that drama over at SheKnows.

Ohhhh, here’s an extra treat for ya. I discovered this while finding that pitch video. This is a video I shot for a crowd funding campaign two months before I shot the above video. The campaign failed because I didn’t have my network of bloggers and PR outlets in place before I needed them.

Consider this a bonus lesson: Have your network in place BEFORE you need it; I learned that one from my buddy, Emmy award-winner, Mario Armstrong. Here’s the crowdfunding video:

And here’s a crowdfunding cheat sheet prepared by a friend who crushed TWO Kickstarter campaigns.

3. Family and their support really matters

I can’t underscore this enough. I mentioned depression in my last point and it’s the under belly of entrepreneurship; it’s something a lot people don’t talk about. The focus is usually on how sexy it is to be an entrepreneur.

Here’s a great article by VC, Mark Suster, about de-stigmatizing depression.

Not trying to get all dark, but I’ve been there. And I know if it wasn’t for my immediate family, especially my wife, Ayana, and my twins, it could have been A LOT worse for me.

Thankfully, meditation allows me to avoid and manage anxiety. I have received suggestions from some people that I try to incorporate CBD oils into my diet, which can also help with calming the mind and relieving stress. Maybe I can try it along with my meditation practice soon. Without meditation, some days I would be an anxious mess. This can lead one down the rabbit hole when things are not going well with the business. If it weren’t for meditation, perhaps, I might have as well looked for buying things like marijuana, from places like bmwo. That too can be done, right?

4. Authenticity matters

This is more of a general statement, and sort of a pet peeve of mine. Especially as it relates to social media. Naturally, there is a lot of good, authentic content out there, but I think so much of it is just click bait and junk.

5. Persistence, more so than patience, is a virtue

Yep. I can’t stress this enough. So many well-respected people insist that persistence is the “X” factor for entrepreneurs. Since most businesses fail the first few years, perhaps there is a dearth of persistence among entrepreneurs.

Thankfully, persistence is the one thing I’m really good at. So maybe I have a shot at this entrepreneurial thing.

6. Sometimes you gotta eat a big bowl of $h!t and pretend it’s peanut butter

I don’t even know where to start with this one. I don’t wanna throw anyone under the bus, so suffice it to say, it’s important to be ok with not getting what you want, when you want it, and having to make do with way less than ideal circumstances. All while staying focused on your goals.

That goal-focus part is key because it does get better. And every once in a while you get to eat a nice gourmet meal instead of bowls of $h!t. 🙂

7. You are stronger than you know

This is the truth. This chart shows the ups and downs of my WeMontage experience:

Screen Shot 2015-02-01 at 9.10.51 AM

Those downs really had me down sometimes, but I got through it and raised another $100,000 in investment capital.

Just know, you too can tolerate more than you think you can.

8. If you realize your greatest fears, lean into them. You will emerge from that experience unafraid and emboldened

This is one lesson for which I am most thankful. I am no longer afraid. Period.

9. And finally, this:

Like a Duck

I learned this lesson from my first startup attempt, which failed because, well, I wasn’t so much like a duck.


That’s all I got. 18 lessons I’ve learned along this amazing journey.

As I learn more, I’ll share more.

What are some of your best lessons you’ve learned as an entrepreneur?

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Feature image credit: Aaron Osborne Great quotes about Learning and Change


  1. Like you, I definitely have had some of my finer moments when my back was against the wall in the 11th hour here and can definitely agree with that and so much more!

    1. Right on, Janine. It’s funny how that works. Most folks are too afraid to go to the wall, I think.

  2. As with Part 1, this all rings true.

    Authenticy – so much! Not just social media for me, though – your product, your vision, your ethos, your customer service. If it’s not authentic, it’s hard to do.

    Great series – best of luck with your business!

    1. Right on. And yes to everything you said about authenticity – it matters. Thanks. You too.

      Hope to see you again soon.

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