A little over four years ago, SureSwift was just a couple of co-founders with an idea. Today it’s a rapidly growing portfolio of more than 30 online businesses, managed by a fully remote team of 80 people working across 14 timezones. Hear from co-founder and CEO, Kevin McArdle, about how we got from there to here.

Usually you’ll find me on this blog interviewing our portfolio of founders to share their stories of building bootstrapped online businesses. I talked to Marvin Russell about how he built an SEO lead generation tool he used for his own agency into the $40k MRR SaaS business, MySiteAuditor. I chatted with Nicholas Firth-McCoy and Tristan Gamilis about the challenges of running multiple early-stage startups, and why they ultimately chose to sell their freelancer time tracking and invoicing app, Paydirt. I spoke with Lilia Tovbin about how she made the transition from having a full-time job and an Ed Tech side hustle, to buying out her co-founders and growing HelpTeaching to scale for a 7-figure exit.

Today I’m turning the tables, and sharing the story of how I became an entrepreneur, and how we built SureSwift into the company that acquired those businesses from Marvin, Tristan, Nick, and Lilia, and gave dream exits to more than 30 other independent, bootstrapped founders.

My Winding Path: From Math Teacher to Entrepreneur

You could say entrepreneurship runs in my blood. My grandfather passed on some major investment opportunities, including one in a new football team called the New England Patriots. Seeing this, my father started several businesses during my childhood, but he never did hit it big.

I wanted more stability, but after putting my Mathematics and Secondary Education degrees to work as a High School Math teacher, I found that effort and merit seemed to have nothing to do with pay and results, and I realized it wasn’t the right field for me.

My next role was at Cerner Corporation, a global provider of healthcare software, where I worked my way up to become one of the youngest VPs in the history of the company. I also got my MBA during my time there, and that’s when I really developed the entrepreneurial bug. But although I had the itch to start my own thing, I never had the right idea.

Eventually, I faced the choice of staying at Cerner, taking a position with a competitor, or starting up a medical device company with a doctor I’d met in Victoria, B.C..

I sought advice from an acquaintance, Don Wharton, who had co-founded three successful companies, to help me evaluate each opportunity. After several meetings, he said, “I don’t want to make your decision more complicated, but I have an idea for a company, and you’d be perfect to run it.”  That idea became SureSwift, and I never looked back.

What Does SureSwift Actually Do?

To put it simply, we acquire bootstrapped, online businesses, and then we take them to the next stage of growth — so in business terms, we’re a holding company that exchanges capital for cash flow.

But our mission, and the thing that gets me out of bed in the morning, is to create dream exit opportunities for independent founders so they can move on to their next great idea.

Because typically, the founders we acquire businesses from are selling because they have a new idea or project they want to focus on, but they want to find the best home for their customers and their team before they move on. (And yes, the big payday of an exit never hurts, but we find that isn’t always a great founder’s primary reason for selling.)

What Specific Kinds of Businesses Does SureSwift Buy?

We started out acquiring content-based websites that made money via advertising. Within the first year, we realized Software as a Service (SaaS) had a greater upside and you could control and scale the business with much more precision, and our focus now is on B2B SaaS.

A few highlights from our portfolio include:

  • DocParser: Automation software that replaces manual data entry
  • ChargeStripe: An app that turns your smartphone into a pocket payment processor
  • BackInStock: A Shopify app that increases sales by notifying customers when a product they wanted is back in stock
  • Storemapper: A store locator app that helps retailers connect customers with their products
  • BigContacts: A CRM and email marketing platform for small business

What’s It Like to Run 30+ Startups at the Same Time?

Running any business is hard. Running more than 30 distinct internet businesses is extremely hard. We excel by taking a data-driven, lean, and scalable approach. Any success we have or lesson we learn in one business gets translated across the portfolio, which leads to very cost-effective growth opportunities.

For example, if we find out having an easy-to-find support phone number is a major win when it comes to building customer trust, we put one on all of our apps’ sites. When we tweak a blog design to optimize for free trial signups and find something that works, we do it everywhere. We use the same services, and a pretty consistent tech stack across our portfolio, too.

We approach talent the same way, sharing it across the portfolio. Our Finance, Accounting, HR, and Tech Teams are centralized, while positions like writing, design, and marketing work across several businesses.

This allows us to operate and grow with a remote team of 80 people (or just 2.5 people per business) working across 14 timezones. Our “Remote First” model is a major innovation with a lot of benefits. It makes us more productive — we measure results, not face time. Diversity is built in because we hire across the globe, and everyone loves the flexible hours and lack of commuting. Being remote also saves the cost of office space, and allows for 24/7 customer support.

And of course, when you grow this fast, sometimes things get a little crazy. But we make it work by being sure to hire people who can thrive in an ever-changing, startup mentality.

Kevin McArdle, Co-Founder and CEO of SureSwift Capital, on Twitter

What’s it really like to run 30+ startups? You can find me on Twitter @Kevin_McArdle to find out more.

What’s Next for SureSwift?

It’s been a crazy and exciting journey over the last four years, and I can’t wait to see where the next four take us. In general, we plan to continue growing our existing businesses, acquiring new ones, and adding talent to our team. A few specific things coming up that we’re excited about are MicroConf Europe in October. It’s one of the best gatherings out there for indie makers and we’re proud to be supporting it as sponsors this year. We’re also digging our new partnership as investors and mentors with Earnest Capital, which gives bootstrapped startup founders who aren’t looking for an exit better funding options. And we’ll be linking up with Earnest to host a Founder Summit in Mexico City in March 2020. But the best part of running any startup (and especially 30 of them) is that you never know exactly where it will take you next. If you’d like to keep up with us, give us a follow on Twitter.