Lessons Learned On Our Journey To 1,000 Paying Customers – Part 3: The Future

This is the third part of our mini-series about what we’ve learned on our bootstrapped journey to 1,000 paying SaaS customers. You can check out the complete series below – so I’d suggest reading the first two articles before getting into this one.

  1. Part 1: The Best Decisions We’ve Made Along The Way
  2. Part 2: The Biggest Things We Got Wrong
  3. Part 3: The Challenges That Lay Ahead

So, this post brings us to the end of the mini-series. I’ll be talking about the things that keep me awake at night as we continue to grow, and the fear of the unknown problems that might be sitting and waiting around every corner. This might be the end of the mini-series, but it’s hopefully just the beginning of our life as a successful organization. Without further ado, here are the things that I’m most afraid of in our immediate future:

Losing Our Culture

This is really the biggie for me. Even if things don’t work out for us at some point in the future, to this point I can confidently look back and say that regardless of the outcome, it’s been worth every single moment. The main reason for that is the sharing of the journey with my colleagues and my (now) friends. We managed to maintain a culture of near total transparency and openness with each other. But every day, as we add more people to the organization, it gets harder and harder for a bunch of reasons including:

  • Our 3 geographical locations
  • New staff members that I don’t get to meet for months
  • Self-imposed pressure from growth targets

In an ideal world, culture would be entirely self-sustaining, a tidal wave that would carry everyone along and not require any one or two individuals to really inject into it to keep it going. But the reality doesn’t quite feel like that yet. I have bad days as anyone does. Days where all I want to do is get my head down and do some coding or something menial. And those are the days that I feel the most guilty. I feel as though every moment that passes where people aren’t smiling or having fun together sets our culture further and further behind.

Of course, the reality isn’t like that at all. Culture might not be a self-sustaining tidal-wave, but it’s also not something that disappears overnight. But that feeling I get on those darker days reminds me of how fearful I am of losing this thing that I (and I think many others) hold so precious.

A few weeks ago, I asked people to write an honest review of their experience working at the company on Glassdoor (you can check out what people wrote here if you like). The overwhelming positive theme was the culture of openness and inclusion.

What we’re doing about it

As always, I don’t want this article to be just about reflection. I want to include some specific tangible actions that we’re taking to address each of these future fears. Hopefully, that might help anyone out there who resonates with the journey we’re going on.

In this case, there are a few things we’re doing to try to minimize the impact to culture as we grow, so I’m going to highlight just a couple:

  1. Local autonomy
    One of the nice things about having 3 offices, is that we can act more like 3 groups of 10 people, rather 1 group of 30. We took a very conscious decision to empower each office with a local CEO (Eric in Korea, Carl in the USA, myself in Sydney). That CEO has full autonomy to make decisions, run their own P&L and even build their own micro-culture under the values of our broader one. It’s a bit of a cheat, as there’s only so long you can do this for before running into inefficiencies, but for now, it’s working really well and is something we plan to continue for the foreseeable future.
  2. Open-door meetings
    This was an awesome suggestion from one of the team. In the early days of the business, everyone would attend ‘strategy’ meetings simply because we were so small. Then after a while, once we got our first meeting rooms(!) – we started to make these meetings more and more exclusive. It made sense, we couldn’t really afford (or fit) 15 people to jump in a room to talk about strategy every week. The actual running of the business would grind to a halt. But still, it felt wrong to be sitting with one group behind closed doors, whilst ‘everyone else’ sat outside and kept working. So we’ve recently introduced an Open Door Meeting policy. It’s a shared Google Calendar that everyone has access too. And any meetings that relate to product strategy, sales or anything broad like that get added to it. Then, everyone in the company gets a reminder 10 minutes before the meeting, and if they want to attend, they can. Even if they’re just interested to see what it’s all about, they’re welcome to sit in quietly or participate. We’ve set the expectation that people still need to manage their own time and get their work done. We’ve literally just launched the policy, so I’ll report back in a future blog post about how well it works out.
  3. Staying hands-on
    This is perhaps a bit more personal. But I’m pretty clear on the fact that I don’t want to be one of those CEOs who spend their entire day talking or in meetings. I’ve made a conscious effort to stay close to the day to day aspects of the business. Some days that means doing a bit of coding, some days I’ll be building IKEA desks. It’s something the entire senior team also do, and to be honest it’s actually quite good fun. The side benefit is that it keeps us as close as possible to our people.

Not Always Being The Scrappy Underdog

If you remember from the first part of this mini-series, we’ve taken a certain pride in the way that we’ve built the business with minimal resources and fighting against huge odds of success. We love being the small Australian startup that beats out competition from much more established software platforms to be the heart of your company’s new strategic plan.

I noticed a couple of days ago that we’re sitting in the number one spot on G2Crowd’s ranking of the best strategic software platforms. We have a rating of 4.7 stars out of 5 and nearly double the number of customer reviews of the next player on the list. They even went so far as to name us one of the top B2B startups in Australia in a list alongside giants such as Atlassian (valued at over $10bn), as well as Canva and Moodle (both valued at over $1bn).

All awesome stuff right? And yeah, it really really is. But it’s also scary. It feels a bit like we’ve been playing around having fun with our mates, only to suddenly realize that we’ve been playing on a tiny platform that has risen into the sky and we’re now surrounded by a 100ft drop in every direction. Don’t get me wrong, we’re in a way smaller league than the companies I mentioned above (waaaay smaller). But if you’ll pardon the language – shit just got real.

So specifically, where does the fear come in? Here are just a few ways it hits home:

  • Is our tech platform everything it needs to be to compete at this scale?
  • Do we have the depth of talent in all parts of the organization to win?
  • Will our customer continue to renew at a high rate?

The list goes on.

What we’re doing about it

The main thing we’re doing to combat this is trying to find a balance between pushing for growth, vs not making growth our master. That meant reducing our revenue target for the year, even though we knew we could probably make it if we really tried. Instead, we put extra resources into the platform and the product. It hurts, and I’m sure some of the venture capitalists out there would be appalled at how casually we adjust our growth targets. But I’m convinced that the main reason we’ve succeeded to date, is by putting the product, platform, and people first.

Being Afraid Of Not Being Afraid

OK, let me try to explain…

As a startup, you kind of get used to being extremely worried about the future. One of the techniques that I think a lot of founders use to manage this, is that they assume they’re going to fail – and if they succeed, it comes as a nice bonus.

But as you grow, and as you build more and more cash reserves, the everyday fears do subside a little bit. Most days they’re just replaced with bigger fears, and indeed one of the best bits of advice I think I could give to any new founder would be to “stop waiting for the day when you’ve made it” – because it never actually comes. The challenges just change and evolve.

But that said, some days – things do actually feel pretty good. Really good. And some days, I even start to relax a little bit and enjoy the ride a tiny bit more. Maybe I’ll spend a bit more money on something, or indulge in a slightly-more-self-congratulatory blog post than usual. And then the come down hits you…and you find yourself being afraid all over again. Except that this time, you’re afraid of the fact that you don’t feel afraid.

If I’m not worried about anything, doesn’t that mean that I just don’t know what I should be afraid of?

Ergo anything could be about to happen. And I’m totally unprepared!!

If that sounds like a mental-health challenge, then yeah, it kind of is to be honest! And it’s not something I really have a complete solution for yet. On the one hand, I know that fear is a healthy emotion that keeps us safe and is a critical element to success. On the other, I’m not quite sure that I’m ready to sign-up to the possibility of always being afraid.

What we’re doing about it

Honestly….nothing yet. We get through each day and try to enjoy the times when everything feels great as much as we can. I’d actually like to throw this one over to you guys to help me answer the question:

Do we ever stop being afraid of the future? And more to the point, should we?

Let me know what you think in the comments below, or send me an email.

Let’s Stop There…

I realized as I was writing this article that I could go on and on about the different fears I have for the future. And even though I’ve talked a lot about fear in this post, I’m also a firm believer in not letting fear dictate inaction. It’s a cliche, but I’d rather regret the things I’ve done in life (and as a company) than the things I didn’t do. And as such, I’m going to stop this article here, and turn my attention back to building the company, and hopefully getting it ready for the next milestone. I’m not sure when the next mini-series like this will be. Maybe at 10,000 customers – maybe at a 100,000. Or maybe something crazily unexpected will happen (good or bad) and I’ll be writing about that instead. Either way, I hope you’ve enjoyed these articles, and I would love to hear your own thoughts about what keeps you up at night as you go through your own individual journeys.

 

Before you start YOUR journey, claim your FREE 14 day trial of Cascade

Cascade is the complete strategy execution platform and will help you to transition your strategy and much more. Easy to use, incredibly powerful and trusted by some of the largest (and smallest) brands in the world. Pricing starts at $29 per month

Comments
  • Darrell Frost
    Reply

    Brilliant idea to encourage staff to use Glassdoor. Again, another insightful and honest blog which makes prospects and customers feel the essence of Cascade. Nice one Tom.

Leave a Comment

Start typing and press Enter to search

Share via
3 Shares