Bootstrapping a B Corp in a “backwoods” city

10 lessons learned on FMYI’s 10th anniversary

2004. The Summer Olympics were held in Athens, Google had their IPO, Hey Ya won MTV Video of the Year, The Incredibles came out in the theaters, and George W. Bush was Time’s Person of the Year. And FMYI [for my innovation] was born out of a coffee shop here in Portland on January 28th.

It’s been an amazing ride. Although I’m sometimes compared to Chris Traeger when I try to spread sunshine around in gray Portland, I have my fair share of gray hairs that have sprouted up over the years. As I’ve reflected on the past 10 years at FMYI, I started thinking about the top 10 lessons I’ve learned starting a bootstrapped B Corporation in an off the beaten path city:

1. Follow your passion.

10 years ago I had just left Nike where I was a Senior Manager in Corporate Sustainable Development, and set out to reinvent the way teams collaborated online. From a young age, I had a passion for the intersection of design, technology, and how people work together. Dialing up to a BBS from my Apple IIe’s modem and collaborating with people to practicing graphic design on a Mac, and playing around with Unix while developing Internet and Intranet webpages helped me explore my interests. I felt strongly about the power of technology designed to help people work together efficiently and effectively.

Fundamentally, as an entrepreneur, you’re trying to solve a problem someone out there has, while building a business model around scaling your impact to take advantage of a market opportunity. Being passionate about helping people out, the problem that you’re solving, and the market you’d like to grow in goes a long way toward making it easier for you to overcome challenges that inevitably come your way.

2. It takes a village.

It’s a funny thing being a founder, combining the ego of thinking you can do something better, while depending on others around you to make it all a reality. David Bragdon recently summed it up well: “That mysterious blend of arrogance and humility is hard to find.”

I believed strongly in the vision and value of my point of view when it came to online collaboration software. But I knew from day one that I didn’t have all the skills or experience to do it myself who could fully flesh out the plans. I surrounded myself with people who knew more than me on many subjects. Having the right team is critical for startup success, from the amazing staff we have, our partners, contractors, vendors, and clients. When you have a small team, each person makes a big impact. Vendors for example are a critical part of your core team during the time of some big decisions. And most of all, you’ll be relying on the support, ideas, energy, inspiration, and embrace of family and friends. FMYI wouldn’t have happened without my wife, other family members, and friends. No way, no how.

3. Live in the “backwoods.”

For a bootstrapped business started with $10,000 my grandmother left me when she passed away (truly an angel investment), and having not pursued any other outside investment, it’s important to pay attention to expenses. Even if you’ve raised venture capital, wouldn’t you want to increase your runway while keeping the cost of living as low as possible for your team? To see how dramatic the differences can be, check out a cost of living calculator.

For me, Portland is the ideal place for a startup. The cost is lower than other major tech hubs such as Silicon Valley, San Francisco, Seattle, Boston, and New York. But there’s also a thriving tech industry with good news emerging seemingly every day, and business for a better world as part of its ethos. And the livability rocks, from the regional urban planning, to tech-savvy public transportation options, bicycling infrastructure, food scene, beer, and the…

4. Coffee is good.

You’d think that living in Portland I’d be a coffee addict. Not the case. But I did learn to love the smell of coffee, the unique atmosphere in each coffee shop, and the occasional cup of Joe (about as outdated as the Chock full o’Nuts ads). Not only are coffee shops a great place to work from in terms of creativity, they’re a perfect spot to set up networking meetings — a casual setting for meeting new people, out of their office so they can speak more freely, and easier to set up than a lunch or full breakfast.

For me, those early days were a blur of knocking off startup tasks on the to do list and building my network in coffee shops. I wanted to make sure my days were full of interaction having gone from a big company to a one person show. I’m indebted to so many who offered advice, introductions, and jumped on board as early clients. I was a big sponge soaking up knowledge, asking numerous questions of people much more knowledgeable than I. Approaching them for advice put us all at ease rather than me asking for client leads right off the bat. And coffee was a big part of fueling the launch!

5. Design the future you want.

You’ve heard about Steve Jobs’ commitment to design at Apple. To me, design is the process of coming up with a solution and the story of how it works. Add on branding, which is what you stand for and why people should be interested. This is the key to producing something of value that people need, try out, use on an ongoing basis, and buy.

I’ve been a design fan for a long time, from graphic design, architecture, branding, story telling, and an insatiable desire to geek out and try the latest software and apps. It was important to me to build a brand that stood for something (“Empowering teams to make a difference through collaboration”). And design a web application that made project management, contact tracking/CRM, and resource sharing approachable for all. We’ve evolved over time to improve and stay in front of where the market is going. It’s a marathon, not a sprint. This requires investing time in redesigns like when we launched FMYI Version 6.0 and the Twitter Bootstrap based 7.0. And more is coming this year.

6. Get a signature first client.

If you’re one of the early players in a market, or have a revolutionary product or service in an existing market, it helps to get others on board when they see an organization or thought leader they trust behind you. Leverage your past work experience, existing connections, and knowledge of what that client needs to offer something of value.

I’m forever indebted to Nike and its innovation mindset for being our first major client. The experienced gained and the input from their team helped us evolve for the better as other major clients became part of the FMYI family. Thank you, Nike.

7. Stay lean and focused.

Flexibility and resourcefulness are key attributes during the start up phase. They also apply when you’re growing. Check out the lean startup movement and see how lean manufacturing principles can be applied to fuel your growth. As a bootstrapped company, FMYI has to be efficient with our expenses and stay nimble so we can adapt as quickly and safely as possible. For us, this has meant being open to custom development on our collaboration platform, having the majority of our team telecommuting from different cities in the U.S., and staying focused on a few things at a time.

For me, I like to apply the “Rule of Three” when planning to help my focus and clarity of what I’m communicating. Keep your ideas and plans focused on three things. And staying focused is important for getting things done. Ideas are a dime a dozen. It really is all about execution. In terms of my focus, I’ve gone through three phases. In the early days, you’re trying to figure out what sticks with your business model, so there’s lots of meetings, events, and networking. Then, it becomes scaling your results by building your team with recruiting, organizational development, and tracking progress. Now, it’s been important to look into the future and invest time in the next big thing for our market, while taking the time to be a thought leader for company visibility, and giving back to our community of founders while learning from fellow entrepreneurs as well.

8. Be an organically fed corporate pig.

If you’re going to be a corporate pig, you might as well be a sustainable one. Having a commitment to the triple bottom line of people, planet, and profit as a B Corporation not only feels good, but is good for business. One of the best ways to measure your triple bottom line progress is through the B Impact Assessment. And when you become a B Corporation, it becomes easier to communicate your commitment while enjoying tools for growth.

For me, nonprofit and foundation board service has been not only deeply fulfilling, but also an effective way to give back while learning strategic skills that can be applied to your business. I highly recommend giving your time to community organizations. We’re honored to have been able to support collaborative efforts for good, initiatives that positively impact people and the planet, while taking home awards recognizing our achievements. But we’re most excited to see where our work will take us this year and beyond in creating a better world with our clients, vendors, and partners.

9. Keep your body movin’.

Don’t forget about fine tuning your own engine. Exercise, rest, healthy food, spending time to recharge, meditation, hanging out with friends and family, karaoke, or whatever floats your boat. The name of the game is a focus on having good energy, recharging with energy from others around you in your life, quality, efficiency, and effectiveness, because there’s only so many hours in a day and numerous potential things you can spend your time on.

I try to live sustainably and have been better about exercising consistently over the past few years including riding my bike a lot more often. Cycling has become not only a way to stay in shape, but also a fun way to gather change agents together and explore the beautiful roads of Oregon together on group rides.

10. Love conquers all.

Challenges present themselves throughout the entrepreneurial experience. People always say it takes longer than you think to get to the next milestone of your company. And there’s also so many amazing moments to celebrate along the way, from new business, to media mentions, and awards. But what you remember at the end of the day and what gets you through everything is love. Doing what you love. With people you love. While spreading the love. And being surrounded by love. Throughout it all, I’ve tried to prioritize being present and in the moment for evenings and weekends with the family while minimizing non-essential travel. I haven’t been perfect, but I know that the enjoyment of those special moments help all of us. I’m forever grateful for their support and inspiration in making this all happen.

Thank you for taking this trip down memory lane with me. 10 years and over a million workspaces. Last year was our best yet, and I can’t wait to share with you what we have coming this year!

Onward and upward,
-Justin