Connecting the dots
Reflecting on your journey as a founder
“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future.”
— Steve Jobs
The journey of starting and running a business is often described as a roller coaster ride. But I think that trivialises it. One acquaintance, on hearing I had started a company, asked me if I’d sat in the corner of the room and cried like a baby yet!
I knew exactly what she meant.
The highs and lows for most working people are, typically, less extreme than for the typical entrepreneur. From the aspirational cries of: “We’re going to change the world!”, to lows of, “we’re going to fail, and everything we’ve worked so hard for will be lost!”
I’m lucky to have been part of a great startup ecosystem in Edinburgh and have talked to many founders about the challenges of building a startup. What follows is some of my story of living with the pressure, and how I’ve gotten through some of the crises and setbacks along the way.
Starting out
I started my first business exactly one year after graduating from university. I was uninspired by the thought of a software engineering job in a large corporation. I also had a strong hunch there was something better suited for me out there. So I took a break from my freelance work and visited a friend in Los Angeles. Interestingly, I’ve spoken to a lot of entrepreneurs that all say the same thing; there is something about California that inspires and rubs off on you.
The trip did inspire me, and in January 2002 I decided to follow my gut and get started with this dream of creating a different kind of company, one that would be a place of creativity, technology and a great place to work. My soon-to-be co-founder, Julie, was up for the challenge. We found office space, registered our company and got to work on finding our first client.
I didn’t think much about the market or how we’d get new customers. I didn’t consider whether it was scalable or financially sustainable, how much we’d charge, or even what our overheads would be. But, as with every journey, sometimes you just have to take the first step, and hey, what did we have to lose? I simply knew I wanted to create something better than the other options I could see at the time.
What I didn’t realise (luckily) was the scale of the challenge we were about to embark on. Over the next decade I’d experience the extremes of joy and fear, wins and losses, barely surviving one moment and being on top of the world the next.
Reality Bites
In 2006, we were 4 years in. Out of the difficult early years, but something wasn’t quite right. The business wasn’t growing as fast I would have liked, and we couldn’t seem to break through to the next level of growth. We’d go from pitch to pitch, winning some, losing some, and with never more than a few months cash runway in the business. I was getting tired.
To add to the mix, Kathryn and I were just married and very soon afterwards found out we were going to be parents! These early months and years were not easy, and the arrival of a new semi-nocturnal resident brought fresh challenges. Whether it was the loss of sleep, the loss of independence, or the general lack of headspace, I’m not sure. But I was floored. I wasn’t able to operate in the same capacity and with the same energy levels that I was used to. But worse, I felt like I’d lost my vision of the company I hoped to build.
Still, there were clients to please, and bills to pay. I started to realise that building a successful agency would require us to make changes. We’d either have to charge more for the sites we were building or do twice as many. That would involve growing the team, which was a big risk, and there was no guarantee we would be able to scale the leads that were coming in.
The way forward didn’t fill me with energy and passion. I knew there must be a different way through this, but was unable to find it at that time.
I felt stuck.
Back to the U.S.A.
Throughout all of that, I still believed that all of this was part of a bigger journey. I knew I’d gained invaluable experience through taking the business this far, and I’d had privileged access to a diverse range of our clients’ businesses. But I still felt restless, and that I wasn’t where I wanted to be.
Sometimes when you’re feeling stuck, you need to get away from it all in order to gain perspective. I’d heard of a conference in San Francisco called startup school, run by Y-combinator, and I thought I’d apply on a whim. I nearly fell off of my chair when my application was accepted, but the timing couldn’t have been more perfect!
The combination of travel, time away, and being with inspirational people is a great recipe to reconnect with ourselves, our story, and what we really want to do with our lives. Being in the same room as people like Mark Zuckerberg, and Jason Fried from Basecamp (whose company Basecamp was a big inspiration) made me realise that running a product with a global reach maybe wasn’t such a crazy idea. I got excited again about running a company that could make an impact for its customers.
I felt fortunate to be in the right place at the right time.
The right place at the right time
The idea that had led me here, came from solving a problem we had in my first business. One that I’d never have been exposed to without feeling the pain directly. I had learned how to build web applications and what made projects more likely to be successful. It just so happened that cloud accounting was taking off. As it turned out one of the pioneers of cloud accounting software, FreeAgent, were based just down the road from us. Also, the cost of starting up and hosting an app had dropped significantly over the past 5 years.
Back then, Xero was a small startup from New Zealand and had about 5000 customers. Now, there are millions of businesses globally using solutions like Xero and QuickBooks.
We had an idea. Accountants typically focused on the past. As a business, we were more interested in the future and making decisions. I had built up years of experience seeing software products built, and (mostly) fail. I understood the process, the problem and the people needed to solve it. That is usually enough to get started.
Value the journey
Building a company that people want to work for and grow at is challenging and rewarding.
Hearing from customers all over the globe that love our product, and rely on it for their business is still a rush.
I really believe if you don’t value the journey that you’re on, you become very outcome-focused which for me is a recipe for stress and unhappiness.
“In the middle of the road of my life I awoke in a dark wood where the true way was wholly lost.”
–DANTE
Getting lost at some points is completely normal, and even necessary. If you’re experiencing a loss of vision in your place of work, maybe it’s an opportunity to find space that allows for perspective and reflection. Or, time to seek out people you trust and ask them what they see that you don’t. It’s an opportunity to dig deeper to find what’s missing.
Back to the beginning
Simon Sinek talks about “finding your why”. I often look back to a picture that I cut out and stuck up on my wall over 15 years ago. I saw something in this random stock image. Something that reminded me of the power that comes from bringing people together to achieve something together. Starting a business is about utilising the gifts and talents we’ve been given and developing those talents to collaborate and solve problems. There will be ebbs and flows. It’s hard work, but there is nothing like the feeling of achieving something by working together as a team.
Follow the thread
So to the quote from Steve Jobs, you can’t connect the dots looking forward, you can only follow the thread.
Looking back often helps to remind you of how far you’ve come, notice the patterns, what felt right, and what didn’t, and take time to think about where you might like to be in the future.
Questions I’ve found helpful.
- What was alive for you in the past which you need to recover?
- What do you want in the future that you don’t have now?
These are two questions are so great that they are worth regularly coming back to. Getting to the heart of what you really want feels like the key to unlocking so much of all this journey.
So, to my fellow and future entrepreneurs, I offer you this advice: love what you do, take time out to find perspective and always remember that there are others out there who have done it before and who want to help.
It’s great to meet people who love what they do. If you’re running or leading a business where you hope to serve and inspire others, you’re making an incredible contribution to the world.
Colin Hewitt is fascinated by startups, leadership, and the future of banking and finance. He’s the CEO and co-founder of Float. Based in Edinburgh, Scotland.
Thanks
Massive thanks to Malcolm Calvert and Catriona Bane for reading and editing drafts of this article.
