There are no silver bullets. But these are damn close.
This morning I gave a talk to the team at Spothero for their Young Leaders series. Normally I give talks on how to build better products, so this was unique.
I think they invited me because I’ve had “approachable” success. I’m not Mark Zuckerberg. I’m a pretty normal dude — got an above average jumpshot, a wife who’s much smarter than he is, and a couple adorable kids.
But I’ve done a lot of the things I’ve wanted to do in my career, relatively quickly. I helped build and sell a company by 27. I started a multi-million dollar consulting firm by 30. Was a Kellogg professor at 31, and a partner at a venture fund at 33.
When people ask me how that happened, I usually say dumb luck. That’s honestly 90% of it. Needle in haystack opportunities.
But I did identify a few things I did in my career that helped. Hopefully they’ll help you too.
1. Show Up First
I followed a girl to New York in 2004. I got hired as an account manager at a startup doing lead gen campaigns for universities. I made 35k a year, and lived in the crappiest apartment in the world.
I was thrilled. I had made it. I was also terrified.
I didn’t know what I was doing. I was sure everyone else was much better than me. The only thing I knew how to do was try to outwork them.
So for the first 2 years of my career, I went to Starbucks in the morning at 6am when they opened. I would work until 8:30, be the first person in the office.
This gave me an extra day every week to get stuff done. It allowed me to be productive even if my days got derailed by meetings.
Just as important, my bosses noticed I was consistently the first person in the office. Which could have happened other ways, but dramatically accelerated the process.
What did I do with all that time? I did what I call microvation. Microvation is the art of tiny innovations.
Sign up for all the crappy projects — the stuff no one wants to do. Try to figure out how to reframe them in a way that made them more useful. And then make them amazing.
We would do CSV exports to give to clients. I turned them into visual reports that we sent as PDFs.
We started using Salesforce — I learned how to create custom reports for the sales team (which was run by the founders).
I tapped into my former life as a stand up comic to create funny, quirky emails to send clients when their campaigns launched, when they got their first leads, etc.
You can do it with anything. Turn picking up lunch into a lunch and learn series. Turn a slack channel with links into a knowledge management program that collects and documents “the way we do things here.”
Microvation demonstrates you’re someone who sees opportunity in everything, and can get things done.
3. Be the Note Taker.
Nobody knows how to execute. Which is a tremendous opportunity. Execution is simply identifying where you want to go, creating a specific plan to get there, identifying the specific next actions to take, assigning responsibility, and most importantly following up.
The best way to do this is to volunteer to be the note taker in every meeting.
The note taker has a tremendous amount of power inside a company.
Your notes become the record of what happened in a meeting. You literally have the power to shape projects and ideas.
If you’re 23 in a 10 person meeting and say “okay everyone, what are the specific next steps we need to take here?” you might get some odd glances. But nobody will look at you funny asking that if you’re the note taker. Nobody will get upset when you follow up in the next meeting.
Before long, they think you’re gifted at getting things done. Which by then, you will be.
4. Dress up.
This one might sound stupid. Especially in the world of tech where hoodies and white sneakers are the new uniform.
I had a mentor who ran economic development in Colorado. Harvard grad. Black guy who grew up in rural south carolina, was the first in his family to go to college. Incredibly proud guy. Every single day he gave me feedback on what I wore to the office. I asked him why.
“Don’t give people a reason to ignore your ideas.”
It’s hard enough as it is, especially if you don’t come from a place of privilege (i.e. aren’t a white dude in America).
If you dress well, at best they’ll think you’re smarter than you are. Most of the time, they’ll simply ignore it. But they won’t think you’re stupid. And they’ll be more receptive to what you have to say.
I know for a fact as a young guy trying to raise money from wealthy LPs 30 years older than I am, it helps that I dress the way they dress. They spend the meeting listening to my ideas, not thinking about the ironic T shirt I’m wearing.
Forget about trying to make a statement with your clothes. Let your work do the talking.
5. Design is a superpower.
When I was college I dabbled in design. I had a pirated copy of Photoshop and had done some projects in school, but I wasn’t very good.
But I had read a book by a guy named Tom Peters, and he said design and branding were going to be a big deal in the future and it was something I wanted to get good at.
Turns out he was right. In a world when almost anyone can build a startup, good design and the ability to craft a compelling brand are a huge competitive advantage.
It’s also a big advantage for you personally. It makes every document you send, every Keynote you make, every project you work on better.
Being good at design demonstrates you have taste. And people like to be around people with taste.
You don’t have to become a designer. But learn to develop good design sense. Start with your Keynote decks.
6. Work for free.
How did I learn design? I went to our Design Director and asked him if I could design my client’s sites. I said don’t show them to the client — I just want feedback on real projects with real constraints so I can get better. And I did it for free.
For 9 months I did this. I designed probably 50 campaigns. They sucked for a long time. But each one got slightly better.
Eventually they started trickling over to clients as the “B option” in case they didn’t like the good one. Eventually they started going with the B option sometimes. Eventually I ended up having a weird split role with 2 bosses, doing half client services and half design work — always from 6–9am or after work, and always for free.
When you’re young, reps matter more than money. Your portfolio matters more than money. Opportunities to learn matter more than money.
If you can command the kind of prices you want and can get all the work you want, great. If you suck and really want to learn, don’t wait for some golden opportunity to get paid to learn. Start learning now — on real projects with real constraints. The money will come.
7. Master sales.
If you know how to sell you’ll never worry about money.
They’re always the highest paid people in the company. They’re usually the entrepreneurs who are most likely to succeed.
As an account manager, I would go out 1 to 2 weeks a month to visit clients, usually with one of our top salespeople. We had to chain together these ridiculous trips to save money — Seattle to Los Angeles. New York to Tampa and back. So we’d try to cram as many meetings as possible in — some with clients, some with prospects.
I would watch the salespeople, learn how to overcome objections, how to ask for the close, etc. Eventually I started up selling my existing clients on new campaigns, new services, etc. I became the one of the top selling non-salespeople in the company.
8) Become a unicorn.
In the tech world, the unicorn is the person who can design, code, go from an idea to a living thing. They say they don’t exist, but they do.
As a hiring manager, looking for one is probably foolish. But as a career move, becoming a unicorn is baller.
One of the products I had the most success selling didn’t exist until I made it. Our campaigns were all automated emails. The school would give us a list, we’d upload them, turn the thing on, the email blasts would start. But clients wanted to be able to send ad-hoc broadcast messages as well.
We didn’t have that. Mailchimp wasn’t a thing. But I found a PHP tool that you’d host on your own server. I paid for the license with my own money. I installed it on one of our servers. I customized the files to have our branding. And then I started trying to sell it to my clients.
My bosses found out of course, and were pissed. Today most companies have protocols in place to prevent that kind of thing. But clients started asking how much it would cost to use our Direct Mailer, and my bosses forgave me.
There’s a tremendous amount of power in being a one person execution machine. While the world is full of “idea people”, there are far fewer people who can have an idea, design the thing, build the thing (even if it’s cobbled together from 3rd party tools — in fact those are often the best ones), and sell the thing. While it makes it harder for you to talk about what you do, it’s really powerful.
9) Read all the things.
At least once a week I was at the bookstore, trying to learn things that would make me better at my job. Sales, design, negotiation, whatever I could find.
One of those things was CSS. Web standards were becoming a thing, and accessibility was a big issue with universities.
All our campaigns were in flash. Because that’s what the design director knew. And he didn’t want to learn how to do it another way. Clients started complaining. Eventually it came to a head. He chose to quit instead of learning how to do it. I got promoted to Creative Director, with the salary to match.
In about 18 months, I went from Account Manager to Creative Director, my salary had tripled. The previous 8 things all played a role. But the catalyst was my being the only person who knew CSS. Because I read.
I still do this —in my current role at the venture fund I really had to shore up my finance and accounting skills. So I started taking online classes and downloading HBR business cases to work on at night.
Lots of people complain about not having mentors, or a plan from their company to help them learn. But you have all the mentors you need at the bookstore or library or online.
The career ladder isn’t in your office. What you do at night matters.
10. Study management.
So I became Creative Director, and life was good. We got acquired by a private equity company doing a rollup. I was suddenly managing a much larger team than I ever had before.
I got brought in to meet the new CEO, feeling pretty good about myself. But he brought me down to earth.
“The things that made you good as an operator are going to kill you as a manager. Today your career starts over.”
He was right.
Management is a skill. There are strategies and practices to it, just like anything else. You can’t just be a good operator with people skills. You have to learn new skills, exercise new muscles.
Become a student. Submit yourself to the discipline of management.
After the acquisition, we moved to Chicago for my wife’s job. I figured my days were numbered, and I needed to start building out a network here.
The best system I know of for doing this is the 5/25/150 method. It’s basically a spreadsheet with 5 names, 25 names, and 150 names. You reach out to the 5 multiple times per week, the 25 weekly, the 150 monthly.
This approach is how I got to know Joe Dwyer, who was a venture partner in town. I left that NY company to became the VP Product at one of his fund companies. A few years later, I started Digital Intent with him and my other buddy Matt. And a few years after that we started the fund together.
The secret to pulling this off is to truly care about the people on that spreadsheet. You’re constantly looking for ways to add value to their lives, to help them out, to introduce them to each other.
You aren’t worried about when it will come back. You aren’t keeping tabs. You probably don’t get as much back as you put in. But you have 180 people who love you. And you get back more than enough opportunity for a lifetime.
12. Write and talk.
A guy named Craig Wortmann asked me to guest lecture in his class at Booth. I frantically put together a deck, and because I have imposter syndrome I loaded it with way more content than I needed. I put the deck up online after, and it got picked up by Growth Hackers. And then Kellogg found out about it. And that’s how I got the gig to teach at Kellogg.
Putting my thoughts online has led to so many opportunities for our company and for me personally. Going to speak around the world. Getting published. Being asked about writing books.
I have no desire to become Tony Robbins. I love creating and investing in products. But I do realize the power of a platform.
Building your platform amplifies everything else you do. And it’s free.
It just takes the willingness to be brave and put yourself out there.
13. The office is your dojo.
I love work. I love being in an office. I think it’s more than just a place to make stuff.
The office is the perfect place to practice life. To learn what it means to be disciplined. To humble yourself and pursue mastery in a craft over a long period of time.
It’s the perfect place to develop character. Smashed together with a bunch of people you might not hang out with otherwise. To learn how to compromise, how to be patient, how to control your emotions, how to build empathy, how to serve others.
Treat it like your dojo. In addition to your KPIs or business goals, have some personal development goals. One guy on my team realized he interrupts people in meetings all the time. And so he’s actively working in meetings on talking less, letting other people finish, actively listening.
You are molding yourself into something, ever so slowly, whether you realize it or not. Mold yourself into something awesome.
Increase the needles in your haystack.
None of this is a golden ticket. I’m always loathe to suggest “rules” — like I said, most of my success has been dumb luck.
But I do think these strategies can exponentially increase the number of needles in your haystack. They’ll make luck much more likely to appear.
Disagree with any of this? Think there’s things I left out? I’d love to hear what you think.