A Side Project Helped Jumpstart My Career

And here’s why you should start one too.

Two years ago this week I had an idea to start a podcast about startups and the people building companies in Boston. Since then, there’s been 58 episodes and over 50,000 downloads from listeners in the Boston tech community. The numbers are modest since Boston is small, but starting this side project has had one unintentional result — it completely jumpstarted my career.

I’ve been wanting to write a post about the benefits of side projects for a while now, and figured the two year anniversary of starting Tech In Boston would be a good hook to do that. PS. If you don’t want my whole backstory and the history of TiB first, you can scroll down to the bottom and just read the section about why side projects are so valuable.


I had absolutely no clue what I wanted to do when I graduated college, and to be honest, I never took high school or college that seriously.

Up until 7th grade I thought I was going to be an NBA player. Then in 11th grade I was pretty sure I was going to pitch in the major leagues. And then by my senior year I knew I was going to have a career on the PGA tour.

I went on to play Division 1 baseball in college, but about an hour into my first practice I was reminded of the fact that there aren’t many “crafty” righties in the MLB that top out around 82 MPH — and my double digit career ERA proves my point.

Add that up with the fact that I graduated right after the 2008 financial crisis when finding a real job was just about impossible, and I thought a career as a professional caddy might be the best route.

I thought the point of going to college was to get a job.

But every entry-level position in the business world required 2–3 years of relevant experience.

“So wait. You want me to uh, have experience for a job that requires no experience?”

Damn.

So, humbled after four months of job searching and working at a golf course back home, I took a paid internship at a tech PR agency an hour away from my parents house and made the two hour round trip everyday starting in October 2009.

The $10/hour at 40 hours a week helped cover my gas, car payment and I was able to start saving a little bit while mooching off of Mom and Dad.

I had zero interest in tech at the time, but this internship was my ticket to the business world.

I wasn’t one of those kids who had their parents subsidize a fancy unpaid internship in Manhattan or Boston, but looking back, I wouldn’t have it any other way.

After a few months, I was able to parlay that paid internship to a full-time paid gig at the PR agency pulling in $30,000/year. This made it so I could start saving a little cash and finally move close to the city (I put 75,000 miles on my car in that first year).

After another year, I left the agency world and landed a job at Constant Contact, and it was there that I started to get interested in startups.

I had gotten close with the founder of a company from San Francisco called NutshellMail that Constant Contact had recently acquired. I was working on the PR team at the time, and NutShellMail and the founder were basically my “account.” The stuff I worked on everyday.

Constant Contact was starting to evolve from an email marketing company to a multi-product company, and NutShellMail (a social media monitoring tool) was the first piece of that strategy, so it was my job to generate buzz, press coverage and awareness for the company in that space.

I had been working in technology since I graduated college in 2009, but it was out of necessity — not because I loved it, and not because that’s what I wanted to do, but slowly I started to become fascinated with it. Specifically the idea that a few people with an idea could just build something from nothing and start generating customers, revenue and a business on their own. That sounded awesome.

So I started to spend my free time reading blogs by people like Brad Feld, Mark Suster, Dave McClure and Fred Wilson. And listening to podcasts on my community like jason and This Week In Startups and Kevin Rose (bring back Foundation!)

That stuff really accelerated my curiosity around startups, and I eventually left Constant Contact to try my a hand at an early stage startup in Boston.

As a result of being at Privy, I started to get involved in the Boston startup community, meeting local founders, entrepreneurs, investors, and people like me who were working at startups.

And then I had an idea: all of these podcasts I listen to are about startups and founders in San Francisco. There are so many people here in Boston — someone should do a podcast about startups in Boston!

So I mentioned the idea at a few local events, and tweeted it to a few people:

I had an itch to start a side project for a few months but never had anything that I was really passionate about.

Luckily Privy CEO Ben Jabbawy, my boss at the time and now a good friend pushed me to just do it myself, in our office.

Whoa. OK cool. Just like that — side project! I spent the weekend buried in Reddit figuring out how to record a podcast, how a podcast gets into iTunes, how the hell you edit audio, what mics you need and everything else.

And the next week, I interviewed Ben Jabbawy for the first episode of Tech In Boston.

Fast forward to today, and there have been 58 episodes of Tech In Boston, with everyone from Eric Paley, who was an early investor in Uber, Diane Hessan who led C Space for 13 years up until a $100M acquisition by Omnicom, Brent Grinna, investment banker turned founder and CEO of EverTrue, Michael Troiano, former agency guy now CMO at Actifio, Jeff Bussgang, Harvard Business School professor and VC at Flybridge, and David Cancel, founder of Performable and former Chief Product Officer at HubSpot — and my current CEO at Drift.

Looking back two years later, starting Tech In Boston — a side project — was the single best thing I could have done for my career.

Here’s why.

Here’s Why You Should Start A Side Project

  1. It forces you to figure stuff out. When you’re at work, there’s always going to be some things that just are not part of your job description. I’ve always worked in marketing, but before starting Tech In Boston, I had no clue had to do something like purchase a domain, set up a website, create and edit images in Photoshop, record and edit audio, etc. When you’re working on a side project, you’re a team of one, so if you want to get something done you either have to pay for it (but who has budget for a side project?) or figure it out on your own. As a result, I’m a more self-sufficient marketer than I was before, and that goes a long way at a startup.
  2. The only way to learn is by doing. Tech In Boston has taken my marketing game up 100x. Why? Well, I’m still the same guy, but for 104 consecutive weeks now, I’ve had to write a blog post, send an email newsletter, watch traffic grow and dip in Google Analytics, watch subscribers grow and subscribers leave, create ads that work and ads that didn’t work. I’m a better writer and better marketer because Tech In Boston has become the practice (reps and sets!) that I need for my real job. Now, I have an opportunity at Drift to do this for real and at a much, much larger scale. My side project laid the foundation for the marketing and demand gen. stuff I’m doing everyday. The ONLY way to get better at something — especially when it comes to startup marketing — is to do it. You’ll never figure out how to get good at customer acquisition by read blog posts. Imagine you could get six pack abs by reading a book about fitness? Doesn’t work that way.
  3. It gets your brain working on something other than your job. Can’t say enough about using the things you’ve learned at work and applying them to something different and vice versa. A side project gets you creatively thinking about something other than your job — but you’ll start to see the returns every day at work. A side project gives you instant experience outside of work.
  4. You have to create your own network. If you want to grow a side project, it’s all on you — but in most cases, you’re going to need help, whether it’s for distribution, co-marketing, getting customers, finding partners or more. You have to build a network on your own, and those are all partnerships and friendships that can come back and benefit your business and career later.
  5. You are the CEO. Most people reading this post are not their own boss. And that’s not anything bad, it’s just the fact that very few people become CEO’s. Starting a side project lets you be the CEO of your own project. You are forced to make decisions on your own. Maybe you have a side project where you have real paying customers or sponsors? How do you negotiate your first deal? What happens when a customer churns? How do you deal with trolls and haters? At work, these are usually someone else’s (or a whole team’s) problems — with a side project, they are yours.

I can’t say enough about the impact of starting a side project.

Now, you just have to take the first step and get started — by doing that, you’ll already be ahead of 99% of people.

PS. If you enjoyed this post, you should check out what we’re doing over at Drift.

Want to chat? Email me. dg@drift.com