Rob Walling on building and selling a SaaS business

Rob Walling has been building online businesses for years. His latest venture, Drip, an e-mail marketing automation SaaS, has been the standout win within his portfolio of seemingly smaller projects. That’s not to say Rob’s other companies weren’t special, or less profitable, or even less fun to work on for the serial entrepreneur.

Growth is hard

Drip achieved a scale that his other offerings hadn’t reached before and even to Rob, a veteran in this space, found growth challenging. The allure to SaaS businesses, that’s software as a service if you’re not familiar with the term, is quite potent in the startup scene. I’m not just talking traditional funded startups either, I’m talking solo entrepreneurs that have an idea and put the pieces of the puzzle together to grow a software business. What once took a small team of devs, marketing, and CEO-types to build, can be recreated by one person.

Drip achieved a scale that his other offerings hadn’t reached before and even to Rob, a veteran in this space, found challenging

If you’ve been following along with season 3 of The Matt Report (and how could you not?!) you may remember the stories from Justin and Paul, two young Canadians that are actively growing these so-called new-age businesses. Both bring a certain artisanal flair to the game. They’d probably laugh (or cringe) at that statement, but it’s true. In my opinion, over the next few years, we’re going to see the start of more “locally grown” software businesses sprout up.

Quality vs. quantity

I live within a mini-crusade against “get rich quick” web marketers. People that run Facebook ads promising you to land $10-$20k web design leads, and their own website sucks. It’s a poison that dilutes quality work, honest business owners, and just takes away from those of us delivering with integrity in this complex web world.

I know you’re sick of hearing me say it, it’s getting harder out there. It might even be harder to make money in WordPress. That’s not to say it’s getting harder to make the products — tools are getting easier, cheaper, and faster — it’s just getting harder to do it better than the next person using the same stuff.

And while starting a small business might seem easy-ish, what happens when you grow too fast? That’s the lesson Rob and I dive into, on today’s episode. For a lot of us in the WordPress space, we’re accidental entrepreneurs. We launch our  products, and when we achieve product/market fit, we — gasp — start selling more!

In the SaaS world, or at least for Drip, that meant re-investing in more engineers, more servers, and better marketing. It wasn’t just about optimizing for more margin and coasting comfortably, in order to make it work, Rob needed more — everything. That’s when Drip looked more attractive to be acquired.

Acquisition for more resources

LeadPages, a popular landing page marketing company, acquired Drip roughly two months ago. Rob is now VP of Engineering for Drip, and has found a renewed sense of excitement for growing the product, my words not his.

Backed by a bigger team, more resources, and more marketing dollars, Rob has a new chance at growing Drip to become an even greater market contender. Not that it wasn’t before, but imagine what an eager founder can do with more resources has his or her fingertips.

I hate to use the word “interesting”, but it will be, to see how all of this plays out.

Interview with Rob Walling

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The links


2 responses to “Rob Walling on building and selling a SaaS business”

  1. Glad to hear Rob say he’s not as transparent as he used to be about revenue and tactics. I thought I was starting to think I was the only one who didn’t want to share my secret recipes with lurkers and competitors 🙂

    1. Times are changing 🙂

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