The Underdog Mentality: Interview with Jared Doerfler, Golf Entrepreneur and Writer of Perfect Putt
This week’s interview is with Jared Doerfler, the writer behind Perfect Putt, a weekly newsletter breaking down the business side of the golf world. He’s also an entrepreneur currently building Hanna Golf, a company that designs and manufactures golf putters. I highly recommend reading his company announcement from earlier this week!
Jared grew up in Mason City, a small town in Northern Iowa, where he dreamed of playing Division I golf. A self-described “underdog,” Jared overcame the odds and walked on to the golf team at the University of Northern Iowa. Post-college, he worked in medical device sales in Kansas City before moving his family back to Mason City, where he worked as a VP of sales and manufacturing at a company called Metalcraft. Inspired by a lifelong love of tinkering and building (and a fateful trip to the Masters), Jared quit his job last year to go all in on expanding Perfect Putt and bringing his putter company to life.
As I learned more about Jared’s story, I wanted to know: What was it actually like to quit? What guided his decision to return to Mason City? How does he deal with things like self doubt? What’s it like building a company in a small town? What helps him channel trust and self-belief?
We spoke about all of that, as well as:
How writing online teaches important life lessons
Leaning into “dumb decisions”
Learning to do everything yourself (and the struggles of fixing wifi issues)
Validating that working hard works
Note: The following interview has been lightly edited for clarity and length. While every effort has been made to preserve the integrity of the conversation, please be aware that the quotes may not be verbatim but reflect the essence of the dialogue.
Setting the scene:
Where do you live? I live in rural Iowa in a small town called Mason City. It’s a town of about 25,000 people. Better known, unfortunately, for where Buddy Holly died.
How would you describe your occupation? Last summer I quit my job. I had been writing for about two years at that point. I wasn’t making a lot of money but enough to quit, go all in on the writing, and also start another golf project. I’m diving into the entrepreneurship world and starting a golf putter company called Hanna Golf. Last year, my wife and I emptied our bank accounts and bought these two pieces of equipment to see what happened. I now have a shop and two CNC mills (mechanical machines designed to produce a wide range of materials). I’d never even seen a CNC mill before much less run one before doing this. At my old job, I had 85 people on my team and oversaw sales and manufacturing. I was more or less a paper pusher. Every day there would be 10 new NDAs to sign, three contracts to sign, pricing to review for a company that wanted us to agree to crazy terms, etc. I did not find that challenging after awhile, and I started dreading going to work. I have not had that feeling yet, although I've had a lot of self-doubt about what I'm doing. My wife and I worked really hard in our twenties, and she's got a good job, so we're able to take a risk. If it doesn't work, then I’ll get another job and double down on the media side of Perfect Putt.
I definitely get what you mean. It’s a scary thing to recognize, “I don’t love what I’m doing. Is this going to be what I do for the rest of my life?”
Yes, exactly. It was interesting because one of my best friends and my former college teammate was my boss. He's the CEO of Metalcraft, and he’s also my wife’s cousin. That’s Iowa for you. It was challenging to decide to leave, but I still don't regret the decision at all. I’m stressed about little things like money. We have two kids we need to take care of, but it's all part of the journey. When you look at things in perspective, I think it gets easier to digest. Our grandparents had a different way of life than we do, and I doubt they complain as much as our generation does. They had much more challenging lives, but their mission and goals were very simple - they wanted to give their kids a better life. Our mission and goals are almost the opposite. It’s not that we don't want to give our kids a better life, but we've already had good lives. We've been fortunate to go to college and be educated and get to choose what we want to do so it's a little bit different. All that to say - perspective is important.
Walk me through the decision to leave your job. I imagine there are a lot of people reading this blog who are thinking, “I’d love to quit my job, but I can’t.” What ultimately helped you make the jump?
The newsletter
I’ll begin with starting the newsletter because I think that’s important. I can't remember who came up with this, but I love this analogy which you can apply to almost anything in life: You have to park the the boat close enough to the dock to jump. I think it’s important to have some sort of income coming in, or some plan you can double down on if you want to quit your job. I was finishing my MBA about 3 years ago and had an elective to burn so I took “Entrepreneurship and Innovation.” It was probably the best class I’ve ever taken. The instructor told us - “You need to be writing online.” My immediate thought was, “This is a terrible idea for me.” I’m not kidding - I barely passed freshman English in college. I was not good at writing. Online, I had no presence. I had a twitter with maybe 60 followers who were all my friends and an Instagram to share photos of my wife and my kids to my 100 followers a few times a year. This instructor said, “It's important to write online, not to make money, but to hold yourself accountable, to create self-discipline, and to learn to accept criticism from people who you don't know.” He said, “That’s the real world. That’s life.”
If you write online and do a weekly post, you're going to start holding yourself accountable. You will get criticism for your writing. Think about it - every time you read something, you probably don’t agree with everything the person writes. There's very rarely anything that I read that I fully 100% agree with. Everyone will see what you write differently. Some people are loud enough to share what they really think. You’ll hear those criticisms, and it’s interesting to see how you react. Do you get defensive? Do you get negative? Or do you accept it? I decided to take my instructor up on the challenge. I’d already been tinkering with things on the side forever.
It took me three months to get 100 subscribers. Today I have about 10,200. People will talk to me about the newsletter and ask, “What’s the key to success?” There really is no secret potion, like anything in life. The two things that have worked well for me are posting every single week at the same time and creating some sort of funnel, whether that’s through social media or friends and family. You have to be consistent. A lot of people want to start writing, and they'll do a great job for 3 months, and then their kid will get sick, or they don't feel like they have time to write, so they stop posting and there it goes! I remember when our 2-year-old was in the hospital with RSV at 5 months old. I still found a way to post. I didn't sleep. It was not a great newsletter, but I still got it done. I think that's what it’s all really about.
Hanna Golf
That backstory on the putter company goes back to college. My golf coaches told me I’d been using the wrong putter and had me use this putting software. My coach went to his office and picked up this weird-looking mallet putter. I tried it, and it ended up working really well for me. It was a prototype so I gave it back to him when I graduated. I'm 35, and it’s now been 13 years since I had that putter. Every single year I would go on ebay and try to find it, and I never could. Three years ago I had my brother-in-law create a similar model of it for me in CAD. I found a CNC shop to make it for me, and I loved it. Then I went to the Masters last year, and I just knew that I wanted to double down on golf. That’s really not when you should make a life-changing decision, but my wife and I talked about it for 6 weeks or so afterward. It just seemed like the right time. We were getting older and about to have our third kid. At some point, life gets in the way and you can't do these things. I didn't do a lot of great things in my old job, but I did build a really great team. The work wasn’t hard because the team was excellent. I did have golden handcuffs and made good money, but I couldn’t ignore the need for a new challenge.
It could be the dumbest thing I’ve ever done, but we really don’t know what’s going to happen in life. I could walk out of my shop today and get hit by a bus. I don’t want to be on my deathbed wishing I would have started a company. My dad also has multiple sclerosis. He retired last year, and I just see how much the disease has affected him. He can’t do the things he likes to do anymore. We used to go on long bike rides, ski, and play golf. He can’t do those things anymore. I don’t know what’s going to happen in life, but we're fortunate enough to be able to do this, so I’m going to give it a go and try.
I have a little bit of income from the newsletter. My wife has a good job. We've decided to give this thing a 3-year window. What’s the worst thing that can happen? I don't contribute to my 401k for three years. That's the worst thing that happens, and that's not a big deal. I’ve got a lot of self-doubt, but I’m happy I’m trying.
You alluded to this a little bit at the beginning, but I think from the outside looking in starting a company can sound much more glamorous than the day-to-day reality. You’re now about a year in - what’s your honest experience of the ~first year of starting a business?
No one is going to figure things out for you. In my case, I'm teaching myself how to use a CNC mill. I’ve watched thousands of hours of youtube and read a bunch. That was super challenging in and of itself. I’ve also had to teach myself how to use CAD. I feel like I had the business side figured out. I know all about distribution, strategy, pricing, and supply chain. Learning how to actually make the product has been the tough part. There are not a lot of entrepreneurs in my town. The ones that are here are mostly in trades. There’s nothing wrong with that, and I have so much respect for those people, but it’s different than what I’m doing. I don’t have a lot of people I can ask for help and support.
There are also no machine shops near me so there’s no one to ask when I have problems with the CNC mill. I remember a month ago, my machines wouldn’t connect to the wifi in my shop. I had the password correct, and it just wasn’t working. I was having a meltdown over it. Of course, it turned out that there should have been no spaces in the username. At that point, I just realized, “I’m out here on my own.” You can't ask your boss for help. You can't go to the IT Department for help. You have got to figure every single thing out if you're doing it by yourself, and I think that's the most challenging part. I think if I’d realized that earlier, my mental state would have been better.
You’ve mentioned self-doubt. I think that’s something every entrepreneur can relate to. What have you found helps you shift on a tough day where it feels like the doubt is hitting really hard?
I’m an extrovert, and it’s tough being alone. I don’t need to be around people all day long, but I really do feed off of other people’s energy. Doing this by myself — it can be really hard to make a shift on tough days. Perspective, I think, is important. I also listen to a lot of podcasts, and I think it's comforting knowing that no one really knows what they're doing. It’s important to remind yourself of that.
I think one thing that is true in golf, but also very much true in life is that if you get frustrated before you start seeing results, the results are likely never going to come. There's this element of building trust and self-belief before that external validation is there. What did you find helped you access trust and self-belief, especially in the early days of the newsletter, before that external validation was there?
Early on in the newsletter, I had a couple of people that really helped me out. It validated what I was doing. I would get a message from somebody who was a lot bigger than me, and they would tell me I was doing a good job. Often, they would help me out and help me grow my subscriber base and following.
As far as the putter company, I don’t know if I’m there yet if I’m being honest.
What keeps you going in this early stage when you don’t feel like you’re there yet? What’s the spark of motivation keeping you going before the belief kicks in?
I love building and creating. I've been an underdog my whole life. I wanted to play Division I golf and ended up having to walk onto a college team. I'm not the most talented golfer by any stretch. I'm not the smartest person. I have to work really hard. From a motivation standpoint, I just want to create a really good product, be able to replace my income from before, and create a small company that’s able to shake things up in the space and provide good opportunities for future employees.
When I quit my previous job, there were people at work questioning my decision. But it doesn't really bother me, because again, I've had that my whole life. Being an underdog is nothing new for me.
You played golf growing up and, as you mentioned, ended up playing in college. What have you learned from golf that has translated into the bigger picture of your life?
Well, golf is just like writing. Golf is just like trying to operate these machines. You'll go to the range and you'll have a great day. Then you'll play the next day, and you’ll play terribly.
I'll have a great day writing and produce a great piece, and then I won't have any content for a week and a half on Twitter or Linkedin. The self-doubt sets in: “Why am I not tweeting more? Why am I not writing more? There's another person out there. They’ve got this piece and that angle. Why didn't I get that? Why wasn't I smart enough to think about something like that?” Golf mirrors life to a tee. It’s hard yet we still come back, and we continue to love the game.
I want to go back to something that I enjoyed hearing you talk about on the Downrange podcast, which is that you were very intentional about moving back to the town where you're from. What led to that decision and the choice to create this unique life where you’re deliberately building your company from your hometown?
After college, I moved to Kansas City. I went to Northern Iowa and my wife went to Drake. She’s a pharmacist. After college, she needed to do a residency and wanted to do something out of Iowa so we ended up in Kansas City. We were there for 5 and a half years, and we loved it. My wife and I dated in high school and grew up in the same town. We started talking about having kids and the kind of place we wanted to raise them in. There were a few things that were the final straw. There was some gun violence near where we were living. Our favorite bar had a triple homicide on it. Then my wife got chased down the street one morning on her way to work. We just decided that if we were going to have a family, we needed to move to the suburbs or move back to Iowa. My dad was getting sick and we’re both close to our families. We just felt it was important to move back home.
We worked really hard in our twenties to be able to afford to make crazy decisions. Not sure there’s ever a right one. So we moved back. We were walking down a weird path in Kansas City. I’m sure having lived in New York that you’ve seen it. We were falling into the rat race. The rat race is basically like, “Look at the car I drive. Look at the house I have. Look where my kids go to school.” We were falling into that and once you’re in it, you can’t get out. You have to work a job to support a lifestyle you don't really want. We were intentional about trying to get out of that. I mean, we enjoy nice things, of course, but we don't need to have them. I didn’t love my job in medical sales in Kansas City. I was really good at it, but it wasn’t challenging anymore. I won rep of the year and then I quit two weeks later.
Some people might not see it as a rat race. Different things are important to different people. I’m not saying we’re right. We’ve been back in Iowa for about 7 years now. There are pros and cons. We live in a very blue-collar town and a lot of our friends have left. If you leave to go to college, most people don’t come back. But again, family is important. Life is short and spending time with the people that matter to you is something we choose to do.
That resonates in a big way. You keep calling them dumb decisions. What I would say is that you have a willingness to lean into what feels right for you and take a chance on that. That’s not an easy thing to do. What do you attribute that ability to? It seems like you and your wife both have it.
My wife is way too good for me. Anyway, I think I’m very naive and that mostly benefits me. I think being naive is important to making decisions and not overanalyzing them. I grew up wanting to play Division I golf. I didn't care how good or bad the team was. That was my number one goal growing up from ages 8 to 18. I practiced every single day to fulfill that dream. My family didn't have money to go play the junior tournaments or get me a big-time instructor. I’m self-taught by my dad and grandpa.
I've seen what hard work does, and I've seen that if you're committed to a goal you can achieve it. The coaching staff in college took a chance on me. It was the best thing that ever happened to me, not because we were a great team or won all these impressive events, but because they validated that hard work pays off. I always go back to that. I know that if I can learn something, I have the work ethic to get it done.
A lot of things we've done in our life have worked out for us because we've been at the right place at the right time and because we’ve worked really, really hard. My wife's more of an underdog than I am. Her dad worked in a door factory for 40 years. She was the valedictorian of her pharmacy school and put herself through school because her family couldn’t afford it. We both embrace that mindset of being an underdog. Our work ethic is what makes us thrive.