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Instead Of Starting A Company I Bought One. Then I Got Hooked & Bought 40 More.

Kevin Mcardle
SureSwift Capital...
from Edina, MN, USA
started July 2015
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Start A Saas Business

Hey, I’m Kevin McArdle, the Founder and CEO of SureSwift Capital. Our ‘flagship’ product at SureSwift is life-changing exits — we buy SaaS businesses from independent founders and take them to the next stage of growth.

At the most basic level, our business model is “buy, grow, and hold.” Some of the names in our portfolio you might recognize are Docparser, Mailparser, Back in Stock (we own several Shopify apps), and MeetEdgar.

We’ve completed 40+ acquisitions since I launched the company with financial partners in 2015. That sounds like a lot now, but it started with just me and my partners — we bought one business, then we bought another. I hired a few contractors to help. It all grew from there.


What's your backstory and how did you get into entrepreneurship?

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 hit it big.

Every phase of running a business is hard, but the challenges you’re facing now just prep you for the next ones ahead.

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 nights and weekends while I worked there, but I feel like I got a Ph.D. in business over my 15 years with Cerner. The combination of those experiences led me to develop the entrepreneurial bug.

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. I asked for advice from an acquaintance, Don Wharton, who had co-founded three successful companies, to help me evaluate those choices.

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 July 4, 2015, became my Independence Day from corporate America.

Take us through your entrepreneurial journey. How did you go from day 1 to today?

The original idea behind SureSwift was really simple. We would pool our capital, buy profitable, internet-based businesses, and roll up the cash flow.

I found our first deals, closed them, and was able to operate several businesses with a very small team of contractors. Back then I was acquiring companies with a lot of different business models — content sites with ad revenue, affiliate models, membership models, etc.

I learned a ton from our first 10 acquisitions, including the hard parts of the web traffic game. For businesses that depended on revenue from ads, I found there was a frustrating lack of control over your destiny because Google controls the traffic (and an algorithm update can kill it) and someone else controls CPMs.

One of my earlier buys was the business MySiteAuditor, an SEO lead generation SaaS business that helps agencies make initial contact with potential clients via automated SEO reports.

With that first SaaS acquisition, I was hooked. The economics and business fundamentals were much more predictable and controllable for a new owner than content sites, and the profit margins made them very cost-effective to run. We’ve been focused on SaaS ever since.

How are you doing today and what does the future look like?

It’s true what they say about overestimating what you can do in a day and underestimating what you can do in a year — when I look back at how SureSwift has grown since 2015, it still kind of blows my mind.

We’ve closed more than 40 acquisitions, and our team has grown to 150+ people (120 full-time, plus contractors) working remotely around the world.

While we started out bootstrapping with our capital, having up-front capital in the acquisitions business is kind of crucial. Once we had data to back up the business model and had refined what we buy to focus on SaaS, we started bringing on investors.

Today we operate two investor-backed funds. We expect the second one to be fully deployed this year. The question of ‘what’s next has been my full-time job since last year. I don’t have a super detailed answer that I can share today, but you can be sure it’s going to involve acquiring a whole lot more great SaaS businesses.

Through starting the business, have you learned anything particularly helpful or advantageous?

The biggest thing I’ve learned is that every phase of running a business is hard, but the challenges you’re facing now just prep you for the next ones ahead. About a year ago I decided to just let go of the idea that things were going to get easier as we grew. (And of course, some things do get easier, but new hard things pop up.)

And the single biggest change I made in running the business was getting relentless about being good at operations. We have systems and processes to help run and scale every single business function — from how we plan work and track metrics for each of our products to how we run departments that span our whole portfolio like finance and HR.

Because we run so many different businesses, there’s just no room for inefficiency in our operations because that ‘one little thing’ on one product or one team immediately gets multiplied and magnified.

What platform/tools do you use for your business?

Some of the apps and tools we use to keep things running at SureSwift and our portfolio companies are:

  • We run our whole company on the Entrepreneurial Operating System (EOS)
  • Ninety for our weekly EOS meetings for each product & department team
  • Slack for in-the-moment communication on projects and socializing
  • Jira for project management and task tracking
  • Confluence for documenting things for our team
  • Jell (which we also own) to run daily standups for our fully-remote dev team
  • Google Docs/Sheets for project collaboration
  • Zoom for calls
  • Zenefits for payroll
  • HelpScout for customer happiness (we use that term because it sets the bar higher than "support" or "success")

Ultimately all of this technology is just a tool that makes our work processes easier, but without the right people to do the work, we wouldn’t get far.

What have been the most influential books, podcasts, or other resources?

Oh gosh, so many. Business is sort of my obsession, so I read a lot of business books for fun and I always try to build chunks of time into my week for reading and thinking. Here are just a few that I always go back to:

  • I love the book The Outsiders. (Not the S.E. Hinton “Ponyboy” one. The one about 8 wildly successful, but unconventional CEOs.)
  • Let My People Go Surfing by Yvon Chouinard, Founder of Patagonia, is another fave — I dig his laser focus on doing right by both people and the planet.

  • A lot of my thinking about the purpose of business, and the kind of company I want to build comes from The Great Game of Business by Jack Stack.

  • Mark Leonard of Constellation Software is my business hero, and I recently read every single one of his shareholder letters dating back to 2007.

  • For podcasts, I always listen to Invest Like the Best.

  • Twitter is where I go daily to hang out and see what the smartest entrepreneurs I know (and the ones I’d like to know) are up to. It’s such a great spot to connect with other founders. (Come find me and say hey!)

Advice for other entrepreneurs who want to get started or are just starting out?

At a high level, I tell everyone that entrepreneurs aren’t superheroes. The successful ones just have an idea backed up by data, work hard, and don’t give up.

And at a more granular level, three things I’ll tell anyone who’ll listen are:

1) Bootstrap as long as you can, especially in the beginning, and only raise if you need to once you’ve proved your business model/idea works and that your business/market makes sense for venture capital or other sources (not all do).

Bootstrapping just gives you a level of freedom and choice you will never replace with a VC-funded model.

2) Listen to your customers and your competitors’ customers. Most founders understand the importance of customer feedback to product decisions, especially in the early days. But a lot of people don’t dig into their competitors’ reviews, which contain a treasure trove of possible competitive advantages.

3) Most bootstrapped founders hire later than they should. It’s necessary and good to work the support desk on your product when you’re moving from an MVP to a stable product you can grow. But if you’re bringing in $50k+ in MRR and you’re still the person answering support tickets, we need to talk.

Are you looking to hire for certain positions right now?

Yes! We’re a global, remote-first team, and we’re always hiring (and side projects are welcome — no need to hide your hustle).

We hire developers in all tech stacks, product managers, customer happiness specialists, product marketers, HR and finance professionals, and more.

You can check out our open positions (or introduce yourself using the “Create your own position” link) and learn more about life at SureSwift on our website.

Where can we go to learn more?

For founders:

For job seekers:

  • Follow us on LinkedIn to be the first to know when we have a role open
Kevin Mcardle, Founder of SureSwift Capital, Inc.
Pat Walls,  Founder of Starter Story
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