Who Is Rob Walling [Part 2]


screen-shot-2016-11-16-at-9-29-14-amRob Walling: serial software entrepreneur. Blogger. Published author. Podcaster. Angel investor. Conference-er. Husband and father.

After the sale of his saas marketing firm Drip to Leadpages last year, Rob Walling and his family since have relocated from the West Coast to Minneapolis.

We sat down for some more random questions to continue learning about him [PART 1]:

What is something you’ve learned about yourself as an entrepreneur since we last spoke?

I’ve learned that I’m more capable of giving up control over certain aspects of the business than I thought I was.

What are the warning signs of burnout for you?

I’ve been coding for like 16 years so I can tell. The first time I know is when I don’t want to go to work anymore, like on Sundays, if I’m dreading a Monday. Other times, when I sit in front of my computer and just have no motivation to get into, that’s a signal.

What’s your antidote?

Well, I think that for me, burnout happens when I’m spending too much time focused on things that really don’t excite or stimulate me. So I’ll go through everything I’m doing on a day to day basis and figure out what I can fire myself from by identifying exactly what it is just sucking the life out of me.

For example, a week ago, we hired a person to assist with email deliverability stuff that’s really critical to our product but that I find no enjoyment in.

A second thing is to take some time to deliberately not think about work…to go out somewhere, to read comics, to do different things.

In part one you talked about founder retreats…

Soul searching is really an ancient tradition. My wife and I began doing it every six months, alternating between solo and joint trips.

When I’m burning out I tend to want to get away from work, that’s a time to unplug and immerse myself in a new environment for at least 48 hours.

With the retreat that’s more a push in where I take the time alone to go in deeper on thoughts but from a different angle on things with new framework of questions and a set of fresh eyes.  I’ve even gone with my cofounder before.

Have you been able to notice a marked improvement?

Absolutely. It’s when and where I set my annual goals, and really take the time to break them down. I have notebooks full of thoughts, ideas, and the stuff that has come out of it.

What are some of your productivity hacks?

I listen to punk music, sometimes just one song looped for hours, which gives me a lot of energy. I only drink coffee in the morning when I work because I want to maintain a low tolerance.   I only do meetings at certain times in the afternoon, and very rarely will take external phone call or coffee meetings. Interruptions are the devil and we built our culture at Drip around reducing interruption, still believing that email is the best way to communicate.

How do you measure your outputs?

It was so much easier in the days that I coded because I knew about how much time each task should take and then pushed to production where you see the outcome. It’s harder to measure outputs these days…I guess the question I’m asking, the feeling I’m going for, is one of keeping ahead of it all and not slowing other people down.  It’s a whole different role and very different to be operating on this level for me.

How much time, money and energy are you investing into investing?

A few hours a month, all via email. Giving some advice, answering questions, making introductions, doing some deal investigations.

I’ve only done nine investments in three years.  The thing about investing for me is it’s easier to get the highs without such lows. I don’t have to live in the trenches and implement, it’s actually refreshing to be advising at a higher level.

What’s something that you’re afraid of?

I’m afraid of not learning, not being stimulated or challenged.  Whenever that happens, it can be a scary time because my lack of motivation leads to either burnout or sub-par products.

How do you avoid those situations?

I ask myself what’s next and go for it! But to get through those thoughts and answer that question is where my retreats, solo or joint, will come into things.

How do you think your entrepreneurial experiences shapes you as a father raising two young kids?

Entrepreneurs see the world differently and so they think differently. There are many paths to get to where you want to be, and can literally go anywhere you point your mind to.

I generally like to expose them to options…options to see the world in all its possibilities. We’re already having college conversations with our 10 year old and encouraging him to think about whether or not he wants to go.

He actually came up with an idea for an ebook about Minecraft that he proceeded to write and we helped him put it online, making a few hundred dollars.

Anything you would like to add in closing?

We are in an extremely unique time right now, because it has never been easier to start a company. Look back 10-20 years and you can see it. Think about 50 years ago….and if it will be this easy in the next 10-20-50 years. It’s a wonderful time to be in business.