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16 lessons from 16 years of GoSquared

Celebrating our super sweet sixteenth birthday

Last year, when we celebrated 15 years of GoSquared we highlighted some of the lessons we’ve learned over the years of running GoSquared.

A year on, we took some time to re-read the post. If you’re in the early stages of your entrepreneurial journey, we may be slightly biased but we’d recommend giving it a look.

If there’s anything we can take from our 16 years it’s that the journey as co-founders, as a team, and as a business is always changing, always evolving.

Sixteen is a great number — it’s a square number, and it’s a pretty large number in the context of company age, and it’s also the age when teenagers start to feel like adults. We still feel young, but as the company is entering this stage of adulthood, we thought we’d share a selection of wisdom we’ve picked up along the way.

You’ve probably read many of these titles before, but we hope the context of how they’re relevant to us will make them a teeny bit more valuable.


GoSquared turns 16

16 lessons from 16 years of GoSquared:

On ideas and building

1. Build something people want.

“Build something people want” is the motto of the most successful startup incubator for a very good reason.

Getting outside the building and talk to customers is a great way to figure out if you’re building something people want. Even if you’re working remotely, getting out of your comfort zone and jumping on a zoom call with customers is the most refreshing exercise in grounding your ideas in reality.

Your customers probably don’t care as much about you as you care about your own business. Spending 30 minutes on a call to see how you fit into their life and understanding their motivations will teach you more about building your product than weeks of internal debate.

2. Share early, share often.

In any team that does creative work, it’s critical to create a safe space for sharing ideas and work. Ideas are fragile and can start in the least expected places. Unfinished work is also fragile, and unless you work incredibly hard to instil the right culture, the cost for any team member to share an idea can easily outweigh the benefits.

The danger with fragile ideas is they can be so easily crushed. Start with yes — don’t shut ideas down before they’ve had time to marinade in the minds of others. One person’s junk idea can be the spark of inspiration in someone else’s brain to come up with something truly great.

3. Constraints breed creativity — embrace them

No matter how large or well-funded your business is, there will always be a desire for more: more team members, more funding, more time, more data. This is true in a team of 1 or 10,000.

Constraints can be viewed as negatives, or they can be viewed as positives — as opportunities to innovate and challenge what’s possible. Something we often refer back to is Patrick Collison’s list of “fast” — a list of projects and products that happened far faster than anyone might expect.

For example, did you know the BankAmericard card (which became the Visa card) was launched and amassed 100,000 customers in 90 days? Often you don’t need more time, you need to reframe the project.

4. The details are not the details, they make the product

One of the world’s most highly regarded designers, Charles Eames famously quoted that the details are not the details they make the product. We couldn’t agree more.

It’s incredibly important to get the basics right, and to fundamentally build something people want, but difference between OK and great often comes down to minute details.

One of the best examples of how caring about the details has led to success was when we put an inordinate amount of effort into our “login” screenMany of these details can now be seen across the web on countless other sites.

On customers

5. Use your own product. Be your own customer

When we started GoSquared we built a product for our own needs, and it was a great way to understand what to build in what order.

It’s not always possible to use every feature of your product, but continuously using your own product, signing up, and experiencing it as your customers do is an incredibly simple, seemingly obvious thing to do — yet so few people do it.

No one knows your product like you do, but how often do you use it like a new user? How does it compare to the high expectations you have of other products you pay for? The more honest you can be with yourself, the better you can make your product for your real customers.

6. Charge the trust battery

We learnt about the concept of the trust battery from Shopify founder Tobi Lütke — every interaction your customers have with your business either charges or discharges their trust battery — a fuel cell filled with their trust in you.

It’s such a simple idea that is so powerful. When you bear it in mind, you make decisions that benefit long term customer relationships, that pave the way for positive sentiment, and you steer clear of so many tactics that can seem like “quick wins”.

7. Your customers are smart — treat them accordingly

The more you get to know your customers the less you’ll think of them as mere rows in your CRM. Each person who uses and pays for your product is smart, and assuming so will likely make you and your team think twice before attempting any quick or dirty tactics.

8. Treat each customer as unique, but scale your process

The days of blanket messaging to an entire customer base ended long ago. It’s no longer OK to send one templated message to all customers regardless of who they are or what their experience has been with your product.

Over the years we’ve learned the importance of treating each customer uniquely (and as a human!), but we’ve also built a process that scales — so we can be personal, while also managing relationships with thousands of people.

In fact, we’ve done so much work on this, we even built our own product from everything we learned. We’re no longer researching and handcrafting emails to every single person who signs up, yet we can focus on applying our efforts on the most impactful interactions when it matters most.

On team

9. Never underestimate what a small group of focused, aligned, motivated people can do

Amazon famously has a concept of “two pizza teams” where a team should be no larger than that which can be fed by two pizzas. We won’t argue about pizza sizing, but we’ve always believed in being smaller, more nimble, and more focused.

We’ve had countless occasions where customers, investors, and friends have assumed GoSquared has hundreds of employees. We don’t! We’ve never viewed “team size” as a great measure of success. One of the great thrills we find is working together as a small team, shipping software that can impact millions of people — the internet offers such incredible leverage to small teams.

It’s perfectly fine to stay small — being a big team isn’t a badge of honour.

10. Celebrate the small wins. Have fun along the way

Anyone who’s worked in a startup or small business will know that there are often many more downs than ups on the journey. It’s not all glossy board rooms and ping pong tables.

There’s almost always an opportunity to celebrate something even when those around you can only see negatives. Tried something out on your marketing site that caused conversion to fall off a cliff? You’ve learned something! Lost a big customer? You’ve learnt something! Pushed a change to production that broke the entire platform for all customers? It won’t seem it at the time, but you’ll definitely have learnt something.

Focusing on an experiment-based process, with a growth mindset was one of the most valuable lessons we learnt from the growth course we did in 2021.

11. Most meetings don’t need to happen

Since going remote, every team has had an opportunity to rethink how they conduct business. Meetings can be incredibly valuable — they can help decisions be made, they can help align everyone around a goal, they can rally morale. But so often, meetings suck. Meetings can sap the time and energy of the team, and they can have a far greater cost to the business than your most expensive invoice each month.

Don’t be afraid to be brutal with the meetings you have: ruthlessly cut those that are not clearly delivering value, ensure each regular meeting has an owner and a crystal clear agenda. Follow the 2x rule. Try silent meetings.

Remember your time, and the time of everyone on your team is the most valuable resource. This quote from Matt Fox, author of The Hitchhiker Man is a favourite:

“Time and effort can get you anything you want in the world. But nothing in the world can get you more time.”

12. Knowing yourself is a superpower

Every single one of us has strengths. We also each have our fair share of weaknesses. None of us are perfect.

There are very few things more powerful than deeply understanding your own strengths and weaknesses — empowered with this understanding means you can work to address your weaknesses, either by learning, confronting, evolving, or outsourcing the things you’re not so great at.

When a team has a clear understanding of each other’s strengths and weaknesses, including their own, it can be incredibly powerful. Suddenly it becomes easier to know who will perform best in a certain situation, and who is best placed to specific tasks.

Spending 15 minutes in the evening to reflect on your day and understand what makes you tick and what drives you up the wall can be a hugely impactful exercise.

On business

13. Simplicity is a war

The natural tendency for all businesses is to grow in complexity over time. You likely can’t overcome all complexity that may creep into your business as you grow, but it will quickly spiral out of control unless you relentlessly fight against it.

We wrote about how complexity is so hard to maintain a while ago — we liken it to a war you must always fight, and it’s one everyone on the team must know they are fighting.

One of our favourite quotes on simplicity is from American computer scientist Alan Perlis:

“Fools ignore complexity. Pragmatists suffer it. Some can avoid it. Geniuses remove it.”

14. If you think you’re repeating yourself too much, repeat some more

What people think is often different to what people say. And what people say is not always what they do.

Whether it’s in your own team, or your business in the wider world selling to your customers — everyone has busy lives and a lot going on. It’s incredibly difficult to encourage people to follow you — employees, prospects, customers. Not only do they need to hear what you’re saying, they need to understand it, and they need to believe it.

The likelihood is, saying something once will barely be heard, let alone understood, and almost certainly not truly believed.

“Repetition makes a reputation and reputation makes customers.” — Elizabeth Arden (founder of the cosmetics empire)

15. Focus is impossibly hard, but without it you’re doomed

Almost everyone offering advice to startups tells you to focus. They’re right!

But of course it’s not very helpful — if you knew WHAT to focus on more then you’d be crazy not to already be doing it. The hard thing is knowing what to focus on and when to focus on it. For that, very people have objectively “right” answers — instead, you have to have an incredibly deep understanding of your own business, your industry, your customers, and countless other factors.

When things feel unfocused — when your efforts as a team feel diffused, it’s likely because something much deeper isn’t clear. It can feel unnecessary and at times it can feel like you’re going backwards, but getting to the root of why focus is missing can be game-changing.

Is it because people’s responsibilities are unclear? Is it because the current goals aren’t obvious to everyone on the team? Is it as fundamentally deep as “we have too many features and are trying to satisfy too many different types of customers”?

It may seem painful to ask these big scary questions, but it’s incredibly hard to succeed and grow without confronting them.

16. JFDI

A slightly ruder version of Nike’s slogan “Just Do It”, one of the biggest problems in starting anything is overcoming the initial hurdle: to break out of your comfort zone and do something. The default is not change things, to let things exist as they are.

In the words of Steve Jobs:

“Everything around you that you call life was made up by people that were no smarter than you. And you can change it-you can influence it, you can build your own things that other people can use.”


We hope you found this set of lessons valuable. If you’re interested to learn more about the history of GoSquared check out our timeline of 16 years.

If you’d like to know more about the future of GoSquared, help shape it by signing up, or follow along via our weekly newsletter.

Written by
James is CEO and one of the co-founders of GoSquared. He also likes to talk about design.

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