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From Agency CTO to Bootstrapping a Startup


Back in March, I decided I needed a change. I left my job of almost 5 years at a boutique ad agency and spent a little time trying to figure out what was next for me. I ended up as a co-founder and CTO of a 3-person startup, and I wanted to share some of things I’ve learned over the past few months.

I wanted to go with a startup because after working at an agency for 5 years, I wanted to remember what it was like to work on one product, and have the ability to make that product the best it can be, versus the agency world where you’re working on 15 projects at any given time and there is almost never the time or budget to make them as awesome as you believe they could be.

I wanted a small startup because although tech is my life, I also really enjoy many aspects of creating a company. Figuring out how to communicate a product’s value to a skeptical user base, understanding human psychology to develop great UX – these are all things I really love being involved in, and when you’re a tiny startup, you have no choice but to be.

When I say startup, if you have a picture in your head about ping-pong tables, Nerf guns and beer on tap in the office, that’s not exactly what I’m talking about. In fact, it’s not remotely what I’m talking about.

I’m talking very early stage, unfunded startup. The kind where you take a 6-figure pay cut because you believe in the team and the product. The kind where you work until you’re physically and mentally exhausted, and whether your company still exists next month depends largely on you. (Not entirely on you, of course, but you have direct influence over the success or failure of your company.) The kind where you work 20+ hours from your couch in your underpants every day and every few days realize you can’t actually remember the last time you showered. The kind where every moment you’re not working on your startup, even if just to sleep for a few hours before getting up and doing it again, you feel consumed with guilt and worry that you could be losing that one influential user that could make all the difference.

That kind of startup.

My startup, Mass Mosaic, was part of the StartFast accelerator program in Syracuse, NY, where they received $25k seed funding (which may sound like a lot, but it’s really not, when you consider fees for company registration, legal stuff, etc) and access to a small team of developers and some really great mentors. I joined MM with about 3 weeks left in the accelerator program and pushed out over 200 commits and deployed 50 times my first week there.

Side note, HUGE props to StartFast for their fantastic program, and the incredible diversity I saw on Demo Day. We frequently the hear stories about a lack of diversity in the tech space, especially startups, but StartFast had a refreshingly varied mix (about 50% non-male or non-white). I don’t have enough insight into the program to know whether that was a deliberate choice on their part, but either way it was amazing to see. More of that please!

Mass Mosaic is an ambitious undertaking. At its most basic, it’s a platform that lets you exchange goods, services, or anything really, with your friends, family, and community, with heavy emphasis on trading and collaboration (versus a straight buy and sell platform.) We match up things you want with things other people have, and things you have with things other people want.

When I was choosing a startup to work with, it was important to me that the startup contributed positively to the world, so Mass Mosaic definitely fit the bill. Social good has always been very important to me, and the sharing economy is one that helps everyone.

Every Tiny Expense Matters – Try to Be Smart About It

Twelve dollars a month doesn’t seem like much to most companies, but when you’re first starting out, even the smallest expenses really matter. It’s critical that you keep your spending down, but it’s also important to consider that spending in context. If that twelve-dollar-a-month tool will save you more than a few hours a month, you should consider investing in it.  When you have no runway, your time is the most precious thing you have, since the clock is always ticking down to when there is literally no time or money left.

It’s always a tough choice, and you’ll have to decide on a case-by-case basis. Obviously, try to use the free versions of services for as long as you can, but always consider how upgrading will impact your productivity and focus where possible.

You’re Never Done – Ship It Anyway

Discussions around feature sets, messaging, brand voice (ugh, did I really just say that?) can be all-consuming, and you can easily get distracted by obsessively revising and editing and perfecting things instead of shipping software. This has been written about thousands of times before in the context of agile and lean development (“ship it!”), but even when you know it going in, it can still be really easy to fall into that trap.

In this age of data and metrics, it can also be tempting to get caught up in obsessively measuring user interest on a possible thing, versus building a smaller version of that thing and letting user engagement speak for itself. Users don’t know what they want. They think they do, so when you ask them what thy want, they will answer, but ultimately measuring their behavior over  what they say they want will give you far more valuable feedback.

This doesn’t mean ship broken code. MVP doesn’t mean half-assed. It stands for minimum viable product. Getting good at breaking down a product or feature into smaller, self-contained parts will be a valuable skill for you and your team, and will help you in figuring out what your MVP really is.

A Good Team Makes ALL the Difference

You will spend exponentially more time with your co-founders than you will with your loved ones. Make sure they’re the kind of people you can spend 20 hours a day with.

I’m enormously fortunate in that my co-founders are amazing guys who not only understand but truly embrace the idea of collaboration. There are no power struggles, no bullshit. Sure, we don’t always agree on everything (what fun would that be?), but discussions are always respectful and considered, because we’re all there for the same reason – building a great product and a great company.

When we don’t agree, we always voice it, because honesty is core to our personal and professional values, and also because our own experiences may lend perspective – but we also temper that with clarification on how important the individial issue is to us. “Picking your battles” is the wrong phrasing, as it makes it sound more adversarial than it is, but choosing what you’re willing to invest time and energy into really matters when all of your time and energy is already spoken for.

Be Uncompromising in Your Compromise

When disagreements do happen (and they will – plenty of them), it’s critical to not take things personally and not get caught up in bullshit. Your goal should always be to make the product better, but early on, there aren’t many scenarios where compromise won’t let you handle an issue and move on. They want a new feature you don’t agree with that will delay a release? Offer up a middle-ground solution that will take less time and that can put the first part of that feature in user’s hands sooner. Once it’s in users’ hands, their behavior will dictate whether the rest of the feature is worth building out.

Sometimes you may be right. It may turn out its a feature no one wants. But sometimes it turns out that it’s hugely popular. Either way, you and your company win with compromise.

There are tons of features my co-founders want that I don’t agree with. You know what? Right now they don’t matter. And when they do matter, when user behavior is demonstrating that it’s actually a feature that they want, I’ll change my mind about that feature. When we’re all working from the same playbook, it becomes way less complicated.

Automate Early

I believe in releasing code every day, even multiple times a day. I believe I automating everything you can early on, because when you have tests and deployment automation set up, it makes it much easier to deploy bug fixes and small features continually. Putting incremental versions of features in the hands of your user base lets you measure user engagement, and also reduces the time between defect creation and defect detection, which is absolutely critical.

And now, some personal reflections…

Work All of Your Network Contacts – Even if it Makes You Feel Like a Dick

I still struggle with this one. I don’t like asking people for anything, and even though I believe in my company and our product, I feel like a dick when I ask people to check it out, and that’s dumb. I have a decent number of Twitter followers, and every time I tweet a link, I feel like a shill. But here’s the thing – when it’s your own company that you believe in on a fundamental, passionate level, you’re shilling for all the right reasons. I believe that our company can make people’s lives better, so why wouldn’t I want to tell everyone about it? I’m still working on it, but don’t expect me to shut up about my startup any time soon, and you shouldn’t either.

Your First Set of Fanatical Users Means More Than You Can Imagine

No matter what your product is, you’ll find a few users who are outright fanatical about it, and these people will give you strength and inspiration when you need it most.

We have one user named Jill who has decided that she’s going to run an experiment in 2015, to test the hypothesis that abundance is everywhere – the core notion my company was founded on. She’s going to travel the country using only Mass Mosaic to get what she needs. She did this without us asking her to. She believes in it so much that she came up with the idea and created a website for it.

From her site:

The Ramble On Project is my attempt to gather empirical evidence of humanity’s ability to improve its situation simply by the will and resources that we have. I started this journey because I think its time to stop thinking change is limited by our pocketbooks, and start making change happen regardless of financial situation. Starting May 31, 2015, I start on a journey across America with nothing more than a van, a guitar, and my four-legged companion. It is my goal to reach at least one city in all of the greater 48 states of the U.S. and exchange my skills, possessions, or labor in a way that is beneficial to the community or individual, while fulfilling my own needs during my travels. In doing so, it is my goal to educate, provide the tools to unlock all of a community’s resources, and exchange as little money as possible for the entirety of the trip. For the situations that will arise wherein I do need funds, I bring my guitar and my voice, but for community, I bring my hands and my heart. This story isn’t about scraping by while living on the road, or living the life of a starving artist. This story is about uncovering the limitless possibilities generated by communities coming together and sharing their resources. With the help of Mass mosaic, and the participation of you, my fellow humans, we can cultivate community, and begin to live in abundance.

I mean, seriously. Drink that shit up when it happens because it’s absolutely amazing, and there will be times when your own feelings of panic and doubt will be your worst enemy. Stuff like this is the antidote.

I’ve Never Been More Tired in My Life – And It’s FUCKING AWESOME

Well, okay, being tired isn’t the awesome part. I’ve had projects at the agency where I pulled hours similar to this. Weeks and weeks without sleep, immeasurable stress about deadlines and KPI, and so on. Stress and sleepless nights are nothing new for me (or for you, probably.)

But creating something meaningful with people who care passionately about the product is a pretty incredible thing to have the opportunity to do.

And since I told you not to expect me to shut up about my startup any time soon, I’m going to ask you to watch this video and sign up for our site.

And be sure to check out my piece in SC Magazine about diversity in tech. Because reasons.

About the author


I'm a tech nerd from NY/CA now living in Lisbon, Portugal. I run Grokability, Inc, and run several open source projects, including Snipe-IT Asset Management. Tweet at me @snipeyhead, skeet me at, or read more...

By snipe
Snipe.Net Geeky, sweary things.

About Me

I'm a tech nerd from NY/CA now living in Lisbon, Portugal. I run Grokability, Inc, and run several open source projects, including Snipe-IT Asset Management. Tweet at me @snipeyhead, skeet me at, or read more...

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