I wanted to interview him because he is 2009 college graduate like myself, seems to be more successful than most of our peers, and because I thought he’d have excellent insights and advice for Generation-Y.
Our conversation was fascinating and I spent quite a bit of time thinking about the best way to put it into a blog post. I decided to outline the various themes of our interview and post relevant “sound bytes” by Jeff under those themes. I also highlighted sound bytes that are pieces of actionable advice.
On Being Lost and Comparing Yourself to you Peers
Much of my conversation with Jeff was spent talking about how he figured out what he “wanted to do” and how he compared himself to his peers. I know from personal experience that many recent college graduates feel they’re not doing as well as they should be relative to some of their more successful friends. Facebook encourages constant comparison between you and your network and gives an inaccurate representation of how everyone is doing. I wanted to find out if Jeff ever worried about this type of thing and if so, how he dealt with it.
“I think I worried about that [feeling behind] more in college. Most of my peers would take different internships in various industries and I chose to spend my summer volunteering at a boys camp in the middle of North Dakota. I felt like I was missing out on all this stuff.”
“I remember being scared coming out of college. I knew people who graduated and spent 6 to 9 months living with their parents and I thought “I’m not going to be that guy, I’m going to have a job waiting for me when I graduate.” I felt like I was way behind.
“People only post the most interesting stuff on FB and you get this world of fake lives and you think everyone else has it better than me. It’s a lie!”
“I’ve been warped since childhood as far as comparing myself to peers. I was home schooled and most of the people who I know that were home schooled are a little weird, including myself. I grew up going to play sports at the public schools and it would always be like “I was the different kid.” Certainly I could get along with them and they were my friends but I was still different and I was very used to it and comfortable with it.”
On Hustle, Networking, and Living out of your Car
Learning to hustle and network is not something they teach in college. At best, you are encouraged to join a few cubs and attend alumni networking events. After graduation, many of my peers sent out resumes to no avail. Jeff started with some internships in college, but then did something that many people are afraid to do: move somewhere new and live out of your car.
“I had an internship in manufacturing and what I noticed was that people worked very hard in manufacturing, they had a high work ethic, but a low change ethic.
I just decided that I wanted to work on a team of smart, intense people that worked hard, and had a high change ethic. I wanted a small team internally so I could be good friends with them. Externally, I wanted to meet a lot of new and interesting people.
I didn’t know anything beyond that and I was on a search to find it.”
“I finished up at TechCrunch and strung together a string of three to four,1-3 month internships. I highly recommend it if you can afford it. I think I had negative cash flow and pretty much lived out of my car and lived very, very cheaply, but I saw not just different products, but different cultures (company cultures), different locations, and I learned a lot.
“Find the people who are the absolute best at whatever you want to do, and convince them by hook or by crook to let you spend time with them.”
“I made a list of people in Silicon Valley and contacted them through various means and none of them would hire me!”
“I was at dinner at Mint.com and said ‘I needed a job so I could pay rent!’ They said, ‘Hey why don’t you do our Facebook or YouTube marketing.’
Looking back that was a great decision but it was totally accidental. I did well at it and I got more and more clients and before I knew, I had a small marketing agency and a few employees. It wasn’t premeditated in the least. I just kept moving forward and trying to perform very well and it worked out.”
“I see a lot of people exiting college and they’re not quite sure what they want to do. They go back and live with their parents and while it’s not a bad thing, if you’re not sure what you want to do, sitting around won’t help that problem. Go get a job and if you’re frustrated by it, at least you’ll know what you don’t want to do. You’ll probably say ‘here’s a few things I liked and here’s a few things I didn’t like. How can I get a job that moves more towards what I like and away from what I don’t like.’”
“Just bouncing around and getting some knocks and bruises is extremely helpful.”
“It’s also just being humble enough to do jobs that may not appeal to you at first.”
Work-Life Balance
Start-ups have a reputation of working crazy hours. Frankly, I think that’s unsustainable and think it’s strange that many start-up founders revel in it. I was curious to hear how Jeff allocated his time as a start-up founder, husband, and friend. Turns out Jeff works long hours but still makes time for himself and others.
“I spent a tremendous amount of time working, I don’t spend as much as my co-founder.
Now is the time that I want to work very hard. later on in life I want to be able to retire a bit more. If I work 150% harder now, I will maybe get 300-500% in returns.”
“I spent time volunteering at a nursing home and I’d ask the people there ‘what were you really glad you spent time on.’ They all said ‘family and friends’ and that’s something I think a lot about.
I try to make sure I have a date night every week with my wife and have dinner with her. I also make time to spend with friends. I have a list of 6-10 guy friends who I try to call once every 1-2 months and spend time with them.
I also spend one night a week volunteering with a youth group. Every time I do that it reminds me I’m just so privileged. Serving benefits you more than the people you are serving.”
“Many people have this idea that a well-balanced life is like a bento box, with a little time spent doing this, a little time spent doing that.
I don’t look at it as work is here, family is here, and friends are here, and my Christian beliefs are over there. I see them as connected. I see the work as I do as a direct result of trying to glorify God. I see it as a direct result of attempting to make a difference in the lives of people I work with.”
Dealing with Highs and Lows
Entrepreneurship is an emotional roller coaster. I think you can mitigate some of the more extreme dips if you become
more process focused and not outcome focused, but it’s not completely avoidable. Jeff knows firsthand what that’s like and shared some of his thoughts on subject.
“The highs are wonderful! I love adventure, and I get a lot of adventure from my work. Business can be very, very exciting!
People have a romantic view of entrepreneurship, but sometimes it sucks! It’s such an emotional roller coaster. Even if you like what you do it can be boring and rough and it’s not glamorous.
I have two co-founders. I have a co-founder in life, my wife. She has been very stable when things have been tough. We’ll go for a walk and talk it out. She is super stabilizing.It’s great to have someone to talk things through with.
With my business co-founder, David and I we’ll encourage each other when things suck. From David, I need more of the emotional cheerleader. Sometimes he needs me to say ‘take some time off and get a little distance’.
You can’t do it alone.
Identity and Faith
For a long time I wanted to be a Navy SEAL. There was no ambiguity until I realized that was something I didn’t want to do. I can’t say that I have a coherent “identity” quite yet but I’m working on it. I asked Jeff if he felt as pulled together as he looked. I was surprised to learn that his primary identity is as a Christian. I thought of tech start-up founders as spiritual but religiously agnostic (this was not based on any facts or data). Jeff is definitelynot in the midst of a quarter-life crisis.
“My identity comes from my faith as a Christian. That’s the big picture for me. It’s the lense I use to look at the rest of my life.”
“Identity is partially a choice, and partially intrinsic personality traits that you become aware of as time goes on.”
“My wife told me once, ‘You know Jeff when you started the company you were so confident, and now you’re not less confident but you know so much more and you say you know so much less.’”
Definition of Success
I wrote before that the definition of success is simply
“achieving your goals.” Not everyone’s goals are the same. I wanted to find out what Jeff’s goals were and how he defined success.
“For business, it’d be great to make some money. We took some outside investment and I made a commitment to deliver a return on their investment.
At the end of the day, money is validating as a form of “hey you picked something that makes a difference in people’s lives (generally).”
I want my investors to say “Hey I got a great return.” I want my employees to say “Hey I’d work for Jeff again because he’s a leader that cares about me even if it costs him something.” My family would say “Jeff didn’t put the business before us” and my customers to say Jeff didn’t sell us snake oil and he solved some of our problems
Am I going to look at the end of my life and say I served my God and that I lived humbly and I loved my wife and friends and family. And not just love where they feel cared for but actively loved. Not just to make memories but to challenge them a bit, especially my friends. True friends challenge each other.
Book Recommendation
I read. A lot. I figure it’s good practice to read what successful people read. I asked Jeff if he had any recommendations.
The best book I ever read is called “The Goal.” It’s about the theory of restraints. There are a lot of things you can work on at any given point in time. What Goldratts’ book shows is that it’s so easy to work on the wrong things. The first thing you should do is fix the bottleneck. The first step to fixing the bottleneck is to identity the bottleneck.
That mentality is incredibly useful when applied to the rest of life.
Final Dale Thoughts
I really enjoyed talking with Jeff. More importantly, he is relatable. I think many people assume that tech start-up founders are mythical entities who have an innate X-Factor that they don’t have.
