The Adventure

Matt Brand
Tech In Boston
Published in
3 min readFeb 23, 2016

Every time I start a new job, I hope and believe that we can build a winner. I don’t like “losing” in the traditional sense. I’ve experienced “winning” and will constantly be aiming for that. I suspect I’m far from alone on that front. In the startup world, the road doesn’t always lead to the promised land. As a matter of fact, it often doesn’t. Often, the road just ends up leading to the next road which is about to be the case with Dunwello.

Certainly, it is not the ideal outcome that any of us on the team had hoped for but it is one that I’ve come to terms with because at the end of the day, startups are hard and there are a lot of things that all have to work properly, plus some luck, plus some stuff out of your control, in order to get to that promised land.

Any regrets about the adventure? No.

When I interview potential hires, among other things, I always ask the following question: “What are your big 3?” I then go on to explain that I’m asking about the things that the person thinks are the most important for them to have in place to make them psyched to join the company. There is no judgment about the “big 3” and it can be any number of things. The point is, I’m looking to find what’s important to you so that we can make sure that there’s an alignment between your interests/needs and the company’s. Those things might include salary, equity, vacation time, benefits, a domain they are passionate about, leadership opportunities, working with a particular piece of technology, etc.

When I think about my own “big 3”, I see an evolution over the course of my startup career. At the beginning, working on something I thought was “cool” was pretty important. Getting paid at all was neat. I didn’t have a wife or kids yet. I had been doing things with JavaScript since it was born so at the beginning, it was important to work with that technology. Over time, having been part of a number of founding engineering teams, a few acquisitions, the birth of my family, and so on, the priorities have changed a bit for me. As an example, one of my current “big 3” items is having dinner with my kids (as frequently as possible — there are occasionally exceptions).

Some other items for me:

- Be passionate about the domain: I have learned that I’m a much better builder/leader when I really believe and am excited about the product we’re building.

- Love the people I’m working with: Of course, everyone would say they want to love the people you work with. In a startup, you tend to spend more waking hours with those people than your family. I want to really enjoy being around them which, in a professional context, starts with trusting that they can and will do their jobs and trusting that their big-picture goals are the same as mine. When we’re all aligned, things move in a more efficient way and the sense of accomplishment comes more naturally, which I believe leads to more happiness.

With that: I love the group of people on Team Dunwello. We have had some difficult circumstances to deal with over the last few months and this group of people has stayed loyal, worked hard, and given their all to try and get us to where we all wanted to go.

So it didn’t end up working but I don’t regret, not for a second, the time I’ve been able to spend with these people. Obviously we are not actual soldiers in an actual war. Everyone acknowledges that. Hopefully you get what I mean when I say that I have absolutely loved being in the trenches with this group of people, building a product that I am very proud of.

I am proud of what we, as a team, have accomplished and what we have built. Any company should consider themselves lucky to have these people on their teams. There were times when they could have jumped ship but remained passionate and resilient about what we were trying to build.

To Tyler, Hilario, Rosie, Sara, Megan, Tim, and Matt: It has been an absolute honor to have gone on the Dunwello Adventure with you. This road didn’t lead where we wanted, but I’m hopeful the next one will and I hope you’ll be there with me.

I am @realmattbrand on Twitter (there are multiple Matt Brands but I’m the, or a, real one). I love all things startup; particularly early-stage. At my professional core, I am an engineer first. I also write a daddy blog: http://mattbrand.com

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Matt Brand
Tech In Boston

I love writing the first lines of code, building teams, UI/UX, and Daddy Blogging (http://mattbrand.com)