Big News! My New Gig at Trello (and Tough Choices)

Wednesday, August 13, 2014 2 No tags Permalink 5


I’ve got some exciting news to share: I’ll be running marketing at one of my favorite startups: Trello.

Have you heard of Trello? If not, then you’re missing out on a simple, highly visual collaboration tool that will change the way you work with others.

A few years ago when I was at FeeFighters, we started using Trello to manage everything from fundraising to timing blog posts. I’ve been a superuser since then, so when Michael Pryor (CEO of Trello) contacted me last spring about coming onboard, I was really excited at the opportunity to help others discover something I was already passionate about.

Now if you’ve been following my life so far, you may have a few questions for me right now, like:

1)   Wait, what about your own startup, matchist? Are you quitting?

2)   Weren’t you also working in venture capital last year? What were your other options?

3)   Did you ever finish your MBA at Booth?

4)   Didn’t you just get married?

Below I’ll answer these questions (and any more you have) in order to provide insight as well as guidance for anyone going through a similar transition. This is especially salient for entrepreneurs who have to make tough choices about what to do when your startup isn’t doing as well as you’d hoped.

1)   What happened to matchist? Are you shutting down and quitting your own startup?

When you’re an entrepreneur, every day is full of gut wrenching choices. That might sound dramatic, but it’s the truth.  I launched matchist two years ago with the idea of bringing together top freelance web and mobile developers and those looking to hire them for short term projects. My cofounder, Tim and I always envisioned matchist to be a bootstrapped business which would grow quickly because of the value we provided to users. We dedicated ourselves to the best service and building a product developers would love.

We launched in the Fall of 2012 to great fanfare on Hacker News and had over 300 developers sign up in one week. We quickly learned that the supply side of the marketplace (developers) was easy to acquire whereas the demand side (clients) would be more challenging. Over the years we experimented with marketing and sales trying to solve the demand side problem.

For a while, we saw the crazy growth that defines a “startup.” However, we soon began to see problems with the marketplace model. We realized that once the marketplace reaches liquidity (ie every project gets the best developer matches and every developer sees a lot of projects that are exactly what they’re looking) the model would work well, but reaching that point would take a much longer time than we originally planned.

I’m not needed on a full time basis to help matchist grow. We have a small but mighty team running the show, and matchist will continue to thrive as a small business, but not a startup (for the true definition of a startup- see Paul Graham).

It was very, very difficult for me to make the decision to pull away from matchist. It’s my baby and I truly believe in our mission. However, we have always been data driven and the numbers we have tell a different story than the one I imagined.  The advice I’d been given as part of being a good entrepreneur is knowing when to step aside- when this opportunity with Trello came along, I knew it was too good to pass up… the opportunity cost was just too high.

There is nothing more exciting than working with the smartest people, doing something you love, and being challenged. At Trello, I get to do all of these things since I’ve never run marketing for a startup that has raised over $10 million in capital and has over 4 million users. I’m used to building things from the ground up, so when on Day 1 at Trello, I saw we have over 40k Twitter followers it was a totally different ballgame. It presents a challenge and lives up to my motto of “Do something that scares you every day.”

2) Weren’t you also working in venture capital last year? 

Yes- Over the past year, I’ve had the opportunity to work with two great VC firms- one here in Chicago and one out in Silicon Valley. Here again, I had to make some tough choices. I wanted to work in VC during my time getting an MBA as it would help me understand how investment decisions are made on the other side of the table. Talking to and counseling entrepreneurs is one of my favorite pastimes so it seemed like a great fit. When I had the opportunity to work full time in VC, it was a really, really hard decision to say no. I had to take a step back and be really true to myself despite all the prestige, capital, and fun the opportunity presented.

However, the whole time I was in VC I had an itch. All of these smart, amazing people were building startups and all I was doing was cheering them on the sidelines. I had to be honest with myself that despite all the cache associated with being a VC, I would always be frustrated I wasn’t the one building the company. I will be an investor throughout my career, but I’m not ready to stop building yet.

3) Did you ever finish your MBA at Booth?

Not yet- but I’m close! Booth has been wonderful providing flexibility in my courseload as I worked on matchist. While it was extremely sad to watch my classmates graduate and move away to build their futures, I’m extremely happy I’ve taken my time completing my degree. Now that I’ll be at Trello, I’ll finish my coursework choosing classes that will be relevant in my day to day work.

Whether the MBA was worthwhile remains to be seen. I will discuss in a different blog post.

3)   Didn’t you just get married?

Yes- On June 21st, I got married to my Sergey in Chicago. It was the easiest decision of my life.

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  • Nourhy
    August 13, 2014

    Congratulations on everything and keep following your dreams!

  • Hashim Warren
    August 20, 2014

    Congrats! Any chance of a Trello redesign? It’s super ugly, though very useful.

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