‘I Cooked Hot Pockets on Irons’: A Post-Acquisition Entrepreneur Shares 3 Bootstrapping Tips


My name is Mike Jirout and the image above is my view as I write this blog post. It’s three weeks after the close of my first successful tech exit. My company developed Ship Mate, an application to help cruise-goers get excited about and prepared for their vacation.  Our motto is “let’s get shipfaced,” and I’ve been aggressively reinforcing the brand this week.

Over the past three years, we’ve had over 600k mobile downloads and reached #2 in Apple’s Top Paid Travel Apps (behind Kayak), bootstrapping the company the entire way. And by bootstrapping, I mean cooking Hot Pockets on irons bootstrapping. Here’s my advice for fellow entrepreneurs:

People Will Think You’re a Failure (Oh Well)

When I tell people that we bootstrapped, the immediate reaction is often an assumption that we failed to raise money. At SF networking events, people constantly ask, “how much have you raised?” They may as well include their last funding round on their name tag.

It embarrasses me now that it embarrassed me then  to reply to them, nothing.

Why didn’t I raise?

I’ve had many of my friends raise money, hit the end of their runway, and have to move on to the next idea. Often it’s through no fault of their own: bad luck, poor timing, whatever. They’re fine with it. They swung for the fences, came up short, and walked away from their cloud hosting, big data, or blah venture with no regrets.

With Ship Mate, I didn’t want a runway — it’s too much fun.

I didn’t want to simply give up and move on when things didn’t work out.

By funding the business on our own, we get to decide when we’re done.

It worked out perfectly.

We had a few options prior to getting acquired. We chose the one that allowed us to continue building Ship Mate (the business that we love) for the foreseeable future. Had we raised, the deal we chose wouldn’t have been an option.

Right Now Matters (Enjoy the Process)

I learned early on that  growing a business is as much about the experience as the outcome. If I spent all day focusing on the exit that may or may not happen, I’d lose my shit.

ShipmateInstead, I made my dream job – part of me was nervous we’d eventually have to exit.

When it comes to my desired profession, my criteria is pretty simple: (1) it needs to pay the bills and (2) allow me to do fun shit (involving family, booze, traveling, and/or partying).

Enter Ship Mate. My daily life is centered around  vacationing. Instead of having to deal with comps and cap rates and matching socks, I get to work from the park and read e-mails like these:

“I love this app so helpful and ready to use. I’m extra exited for my cruise now. Thank you for what you do!”

And, even better:

“Where the fuck is the carnival dream you nerd?!”

Being Cheap Becomes a Game (Get Creative)

There’s always a way to avoid larger expenses. You’re an entrepreneur – figure it out. Here’s a few examples from our playbook:

Office Space: Even better than coffee shops… libraries. They’re clean, quiet, usually have good internet service, and sometimes the librarian brings you cinnamon cookies.

Employees: We’ve had two UCLA Anderson interns (both way smarter than I) help us for free. We also hired a web programmer for 1/3 of the market rate. Each wanted experience with a promising startup and I like to think that we helped them enter the industry (one just moved on to Amazon).

Hot Pocket

Travel: We got free flights with American Airlines BusinessExtra program and Airbnb’d it when not hitting up a relative for a couch.

Food: Cook Hot Pockets on an iron (you thought I was joking).

Tradeshows: For TechCrunch, we volunteered to set up the event and got in (and backstage) for free. For Launch, we helped a buddy present his company and got in (and backstage) for free. For the biggest cruise conference, we built the mobile app for the event in exchange for $10k worth of booth-space and promotion. (note: If you can’t finagle a free booth, it’s still worth going as an attendee for 1/10 the cost. You’ll have access to the same people).

Business Services: I simply contacted the companies we wanted to use and asked for free stuff. We’ve gotten free services from Parse, MailChimp, Joyent, Microsoft, Tapstream, CloudSponge, and many others. Some we reciprocated value through shared analytics, etc. Others just gave it to us for asking. Even when not free, there’s usually a cheaper / more creative way. For instance, when we needed a video demo, we had bids between $2k and $25k. Instead, for $25 I found a demo video template and had an Odesk-er customize it for another $25. It turned out great.

If you choose to bootstrap, just remember that there’s always a creative way to avoid large expenses. You’re an entrepreneur. You can figure it out.

Doesn’t Bootstrapping Suck Ass?

Yeah, it sucks Roseanne Barr ass. You’re waking up on couches covered in dog fur for three months.

Your business school buddies are making six figures and showing off because they can afford to get haircuts.

You’re trying to bargain with the barista at Starbucks; and, 99% of the people in SF think you’re a shithead because you haven’t raised money. But, then hopefully you’re able to continue doing what you love, you get asked to be an expert on Clarity, and you get to tell your story while watching the sun set and drinking a scotch that you snuck onto a cruise ship (old habits die hard).

Mike Jirout is a serial entrepreneur and co-founder of C Monster Solutions, which was acquired by Cruiseline.com in 2013. His accomplishments include:

  • Conceptualizing and building Ship Mate, a popular mobile application for cruisers that attracts more than 70k users per day.
  • Bootstrapping a business, all the way to its sale.
  • Being taller than most girls.

Set up a call with Mike to learn about bootstrapping, mobile apps, lean startups, and entrepreneurship.

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  • Lucas C McCarthy

    Cool story, where did you quest for video templates?

    • Jirout

      Thanks, Lucas – got the template from VideoHive. Let me know if you want the Odesker’s contact.

      • ThomasRankin

        Hey Lucas. Love the story. I’m from Dan M’s neck of the woods and am building a company on the cheap (for now). Love your comment about doing what you love. Dash Hudson truly is a passion. Would also love the Odesker’s contact as we’re about set to gear up a demo vid.

  • Marcin

    Awesome article, congrats. Can you share some revenue/acquisition numbers? PS. I must try ironing food, maybe pancakes?:)

    • Not an Entrepreneur Either

      …You oughta think on it a little more before trying to iron pancakes.

      • Jirout

        I actually think there’s potential there…

    • Jirout

      Unfortunately I’m not able to mention specifics, Marcin. But, as soon as the ink dried I paid off all of my debt (six figures), now earn a good salary for a post-MBA human three years out, and have enough equity incentive to stay for a while.

  • tomii wu

    yup…sounds like San Francisco. there was a time that city recognized money can’t buy style…

    • Jirout

      I wish I could have seen it then, Tomii

  • Manas Mudbari

    Hi Mike,
    Great article and thanks for the videohive’s info. Also could you please share the Odeskr’s name? We’re thinking about bootstrapping as long as possible as well.