After the sale of his saas marketing firm Drip to Leadpages earlier this year, Rob Walling and his family since have relocated from the West Coast to Minneapolis.
We sat down for some random questions to learn more about him:
When were you born and where have you lived?
I was born in Santa Clara, 1974, went to UC Davis for college. I lived in LA for five years, and have since lived in Boston, Connecticut, Sacramento and most recently Fresno for past seven years. My wife Sherry and our two boys (6 + 10) moved Minneapolis in July after Leadpages bought my company Drip.
What neighborhood did you settle in?
We’re living in Linden Hills – close to downtown and very family friendly.
How does business serve family?
I’ve been very deliberate about making my family life as important as my professional life.
I think business serves family when it gives you the flexibly of time and choice, like work hours and traveling. For example, I can pop out for a few hours as needed so long as the business is getting done at one time or another. I always thought of my business as long term means of supporting my family. Now, with the exit to LeadPages, my kids are setup to have a unique life, to experience things that they otherwise might not have…like international traveling, world class education, and economic opportunity.
How did you get into tech in the first place?
I learned to code when I was 8 years old on an Apple IIe in 1982 when Jobs and Woz were just getting going during the early days of Apple. I went on to college for electrical engineering and was going to enter the construction industry…well I actually did for about a year and a half before I got back on track in tech as a coder in 2000/2001.
I realized pretty quickly that it was a lucrative career but that I also knew I didn’t want to work that way for 20 or more years so I started building products pretty quickly.
I had at least half a dozen failures before, like hardcore all in crash and burn style. I would burn out and rage quit on entrepreneurship. I really started questioning web apps/SaaS and so I went back into consulting from time to time.
Of course I got sick of that after a few years so I branched out again, but this time in a more calculated way. I spent all my savings on buying a codebase called DotNetInvoice that was in alpha at the time. I was able to launch and grow that around 2005 and started making a few thousand dollars/month.
How did Drip form?
Over the years, I have developed an approach of bootstrapping called the ‘stair step’ approach.
It involves launching something and cutting your teeth and getting some experience, and then launching another one. The whole goal was to reach 10K+/mo gross revenue, and I made it there across a few different sites/services. At that point, I was just maintaining the businesses while we had our second child, I spent a year living the four hour work week but after the baby and some time I got bored so I stepped it up.
I acquired HitTail in 2011 for $30,000 and grew it from $1,500/mo revenue to about $300k/year. That was doing well until Google started changing the game a bit and that made me question if I wanted to risk my livelihood entirely on Google.
Drip actually came in 2012 as a marketing feature that was originally developed for HitTail. I found a partner, we made a few hires, and spun that out on its own.
I want to be clear that I don’t come from any money or special circumstances. Each step along the 10 year progression (2005 to now) was hard, painful, risky and expensive. I took that stair step approach and played a lot of small ball to get here.
Were you ever scared?
Absolutely. Specifically I recall when I wired the money to buy HitTail I looked at my wife and just kind of shrugged with insecurity about what just happened as it was all our savings at the time.
She said: “This is what you do, what’s the alternative? You’re an entrepreneur and you can make it work.”
Another example was earlier on with Drip, I had a big burn rate combined with a really poorly timed tax bill. All of a sudden I had way less money in the bank to make payroll and clear my tax liability. In 2014 from April through October was a tough time because I was worried about money that whole time
I thought: “I’m a bootsrapper, this isn’t supposed to happen, this is what funded companies experience.”
How did you work through that?
After the initial panic and the stress, I went on a solo getaway for a few days along the central coast of california and didn’t do anything but soul searching and some clear headed problem solving.
You can’t go 10-20-30 hours deep into thought at any other time because of partners, teams, family, extracurricular stuff. I needed to give myself that time to disconnect from everything and get to the root of issues. And its a method I’ve deployed since then. In fact, my wife went on to write a book around that called: The Zenfounder Guide to Founder Retreats.
You’ve mentioned your wife throughout our conversation. Would you say she has always been supportive of your entrepreneurial pursuits?
Early on she wasn’t. From 200-2005 I was billing out good hourly and then at night I was putting a bunch of time into things that didn’t affect the bottom line. But you know what the stair step did for me? It showed her that it could work, one step at a time. So by the time I was ready to write that check for HitTail, she was on board and knew I could make it work.
So when Clay sent you the infamous acquisition email – what did you think at first?
My initial impression was that we would be a good strategic fit if we were to join forces. We have different approaches towards things…we focused a lot on the product, where as Leadpages is a phenomenal marketing machine. I was wondering if, and how, our cultures could merge?
Clay was more in the marketing space, I was more in the startup space and I think both are a little skeptical of one another, for good reason. But we got over that.
What is MicroConf all about?
I started MicroConf in 2011 as a conference for self-funded startups. The whole purpose is that there was no conference for small bootstrappers to get together, founders who were doing what I was doing and what a portion of startups are focused on – as opposed to fundraising. We now do three per year, two in Las Vegas and one in Europe.
What else are you into outside of Drip/LeadPages?
Podcasting, blogging, and investing.
That’s all the teaching stuff, which doesn’t come without doing the work first.
I’ve invested in 8 B2B sass companies so far
It’s interesting to think that for the first time in a long time I don’t actually own any software right now so I’m having fun with these projects on the side now.
How do you feel now that you’ve sold and are integrating with Leadpages?
Some people have a sense of pride about not selling, they’re very dogmatic, thinking that it means selling out on the product or team, but I’ve never felt that way. Now we have a lot more resources to better serve customers.
Clay was really sensitive to not break the magic that we had created between our product and our customers. Leadpages separates their staff by functional areas, but the Drip team is all together and Derrick Reimer + myself are still running the product team.
Did you know anything about Minneapolis before you moved and what do you think so far?
We visited once for a few days in May. My wife described it as Portland with less pretentiousness. Personally, I like big cities but I don’t need them because wherever my work and family is I’m happy. Minneapolis is a fair sized city. I’m struck by how clean it is, how much the urban planning makes sense, the food and entertainment options. Even the DMV was not a terrible experience.
Who is someone you respect and admire in the business world and why?
The several, and someone who comes to mind is Jason Cohen, blogger and founder of wpengine.com. He just shows up, quietly builds companies, and has created hundreds of millions of dollars in value.
Do you see yourself doing something outside of Drip/Leadpages in the future?
I don’t think I will start another software company in my life. I’ve just done it to the point where I can’t start a smaller one and I don’t have the energy to start a bigger one.
What is something that you’ve learned about business recently?
I think each company has its own zone of genius. I’ve realized that Drip’s zone of genius is product. We build a great product. And Leadpages’ zone is marketing. So now when I look around at various products and companies in tech, I’ve learned to better identify what that and where that zone is.
What excites you about 2017?
Drip’s userbase is growing significantly. Our monthly trials is more than the overall number of customers we had when LeadPages acquired us. I think they’ve quintupled our user base wiinth the first few months. To see where were at with that and where we’re headed is exciting. Aside, there are a bunch of winter sports that my family has never done before so I’m about to embrace the winter!
Any closing thoughts?
If you’re an entrepreneur reading this, don’t buy into the hype of entrepreneurship about raising a bunch of money and going to the moon. If you just do what makes you happy and do it well — you’ll be rewarded.