How I managed to get Tim Ferriss to advise me, launch a product to a huge audience, and take over…

You probably have no idea who Jason Allred is. Most people don’t. He’s a 35-year-old pro golfer who is far from a household name. Golf’s tough, and Jason has had more downs than ups with the game.

“At the end of 2008, Allred had lost his PGA Tour card, then failed to regain it in the qualifying tournament, leaving him nowhere to play in 2009.”

–Mike Tokito

Then he got to play in the 2010 U.S. Open. That was over five years ago. After that? Not another tour event, until all of a sudden he had a couple good tournaments in 2014. Great, right?

Not exactly. A couple good random tournaments doesn’t really mean much for a PGA golfer’s career. Even good, pro players can’t just play in any PGA tournament. If anyone were allowed to try and qualify, the first day of a golf tournament would never end. So only a pretty elite group are invited to most tournaments.

But, there’s a loophole.

These tournaments are sponsored by big companies: Northwestern Mutual World Challenge, Hyundai Tournament of Champions, Sony Open, etc. And with big sponsorships, comes a say in who gets to play.

So, Jason, who wants a lot more from his PGA career, emailed the corporate sponsors of an upcoming tournament, the Memorial. But a bunch of players send these exemption request emails.

Jason took it up a notch.

He also sent pictures of his home life to let sponsors know that he’s not just a golfer, but a real person supporting a family. And he’s persistent. He followed up with another note — this time, handwritten.

Who handwrites anything anymore?

That got their attention.

“He wrote a nice, compelling, personal letter to the exemption committee. And that stuck with them.”

Dan Sullivan, the tournament director

The Saturday before the tournament, Dan Sullivan called Jason and offered him a spot.

Jason took full advantage of the opportunity — placing 15th. Not too shabby. It’s a six figure paycheck and chances for more tour play, all because he stuck his neck out a little more than anyone else to ask for help from people who had the power to.

In high school, I really wanted to play basketball. I tried out for the freshman team. I wasn’t good enough and was cut during tryouts. But my father encouraged me to find the coach at school and ask if I could help the team practice. My father figured they might just need warm bodies to play against, and through the experience, maybe I’d get better enough to make the team someday.

It was nerve-racking. I knew the office where the coach would be at lunch. But I couldn’t get myself to open the door.

I looped around the building a couple times, passing the door each time. I was too afraid to go in. But, knowing I couldn’t go home and tell my Dad I failed to accomplish this, I grabbed the door knob of the office with my sweat-soaked hand, opened it up and walked up to the coach and made my pitch, “I’d love an opportunity to help the team practice if you need anyone?” He smiled, thanked me for coming in.

Then he said, “No.”

Many people would take that as a setback and never try anything like it again.

But I learned a different lesson.

I felt this tremendous accomplishment walking out of that office. I wasn’t going to play basketball, but I just got up the courage to ask someone to help me in a way no one else was asking.

And nothing bad happened. I was a little embarrassed, but I didn’t die from being uncomfortable.

I could ask anyone anything.

Later in high school, I ended up on the volleyball team. Unlike basketball, I was pretty good compared to most of my peers. But by junior year, I hadn’t grown as strong as some of my teammates, so it was getting tougher to stand out from the crowd in ability.

I found myself getting stuck in what they call a “back row specialist” position. This is a good place for a player who is quick and good at defense. There’s nothing to be ashamed of. I was actually really good at it. But I wanted more. I didn’t want to get substituted out every time it was time for me to play offense.

So, I walked up to my coach after a practice and asked him, “How can I get good enough that you’d let me play offense?”

This had the exact effect I wanted.

During practice he’d work me hard in offensive drills and scrimmages. Eventually I got better. By the end of the season, I was one of his starting offensive players.

I’ve been really fortunate on where Draft (a software product I’ve made to help people write better) has gone. But it’s not strictly because of talent or luck. Like Jason Allred, I was initially able to put a few good things and ideas together, but I needed help to keep the project going.

My blog, Ninjas and Robots, has been instrumental in spreading Draft. I got a big audience boost because it was one of the first blogs on Dustin Curtis’ SVBTLE blog network. But it was “invite only”. How was I lucky enough to get one of those invites?

For awhile, I had a guy helping me with Draft. We would meet every now and then about Draft’s product design and strategy. He was the one that pushed for great ideas like “comment out” your writing and little details that have really caught people’s attention. That guy is Jason Fried, the well known entrepreneur behind Basecamp and the publication where you are reading this. And that all eventually led to Jason asking me to take over Highrise and turn it into its own business.

A lot of people keep asking me, “How on earth did you manage to get Jason as a mentor?”

I’ve gotten some other really insightful advice during an hour-long phone call about Draft with Tim Ferriss, who’s famous for his Four Hour books. The phone call led to five action items that immediately improved the product. Not to mention, he’s even recently mentioned his love for Draft on his podcast. How’d I get someone as busy as Tim Ferriss to give me the time of day?

Dustin Curtis, Jason Fried, Tim Ferriss — none of these guys reached out to me saying, “Nate, what can I do to help you?” Why would they? They are inundated with their own lives.

The only way I entered into their orbits was by simply following my Dad’s advice from that time I wanted to make the basketball team:

Open up your mouth and ask.

P.S. It would be awesome to meet you on Twitter, or check out how you can improve your chances of asking for opportunities and following up using Highrise.