I had Daniel Fayle on the podcast this week, talking about how he and his co-founders bootstrapped Chekkit from zero to $2M+ in annual recurring revenue. One thing stood out to me: Dan and his colleagues didn't hesitate to get their hands dirty and make their own luck.

Founders talk a lot about luck. When we’re successful, we are at the right place at the right time. When we’re failing, we dust ourselves off to go ahead and shoot another shot, temping fate once again.

But what is luck — and can we influence it?

I believe so. And I’m not talking about manifesting our destiny through words of affirmation. For me, luck seems to happen when I intentionally work on increasing the size of my opportunity surface. So let’s see how you can grow your own opportunity surface.

Everyone has an Opportunity Surface.

Your opportunity surface is the sum of all the opportunities available to you. It’s like the playing field on which the game of progress is played. The larger the opportunity surface, the more chances you have to win. And it’s not just about opportunities right now —like the deals in your pipeline or the size of your Twitter audience— but it’s the potential of all possible “lucky moments” of your life, past, present, and future.

It’s all about leaving traces of your ambition, ready for others to find and trace back to where you are right now. In many ways, it’s like a spiderweb of markings that lead people who should know you directly to where they can get in touch.

Here's an example from the early days of my software engineering career. I had dabbled and played around with JavaScript (and its now-long-gone CoffeeScript variety) and built a couple of small projects that I publicly shared on my GitHub profile. The code was available for free, I even showed screenshots of my work, and one day, I got a Twitter DM asking me if I wanted to work for a VC-funded startup in San Francisco. Someone in their small founder team had searched for developers using this particular technology, and they had found my practice projects. Two weeks later, I had a job just because I had left a breadcrumb for someone to find.

Your opportunity surface is the area on which chance encounters and "lucky happenstance" will strike. All you need is to provide fertile ground and keep an eye on it. And you can do that intentionally.

Entrepreneurs can use this concept in ways that will benefit the growth of their businesses, relationships, and personal brand.

Do Things that Don’t Scale

One way to increase the size of your opportunity surface is by doing things that don’t scale. Paul Graham’s essay on this is something every aspiring founder should read — and many established entrepreneurs would do well to re-read it from time to time.

In a nutshell, this approach means putting in the extra effort and going above and beyond to make connections and build relationships using methods you can’t sustain forever, for example, by reaching out to potential customers or partners personally rather than sending impersonal emails or messages. This approach might become impossible to maintain in the long term —that’s the whole point here— but it will lead to valuable insights, connections, and opportunities that wouldn’t have been possible otherwise.

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Let's take a quick look at this issue's sponsor, SaaS Origin Stories. ​ ​ In this episode of the podcast, Phil talks to Bryan Clayton, CEO of GreenPal, a lawncare SaaS business. And as luck would have it, Bryan talks at length about the things they did that didn't scale —but ultimate jumpstarted a successful SaaS business— like handing out flyers and canvassing the neighborhood. ​ I was just talking about this! It's a common ingredient in successful founder journeys. The more you look for it, the more you find it when "those who made it" share their strategies. ​ If you want to learn more about early-day tenacity and how to build a marketplace platform that serves everyone involved, I highly recommend you give SaaS Origin Stories a listen. ​ Learn how Bryan bootstrapped GreenPal

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In the first years of building FeedbackPanda, I made a point of quickly responding to customer service requests. But not only did I try to solve their issues as fast as possible, but I also continued to chat with our customers, sometimes for half an hour. Obviously, that doesn’t scale: I’d have no time to run a business if I did that with every customer.

But I didn’t do it with every customer. Just the first few users who showed enough interest in its success to actually reach out to us about the issue they encountered. We talked to the people that pre-selected themselves into our communication channels. That made it very likely that we could learn much from them about their needs and challenges.

And it didn’t just increase our chances of learning more about our users. It also allowed us to connect with them on a personal level — something that almost always surprised them. Not many business owners take the time to talk to their customers. It feels special to be taken seriously, and those early customers we chatted with for hours turned into our most raving fans who brought thousands of new customers to the business.

Diversify Your Inputs

Another way to increase the size of your opportunity surface is to diversify your inputs. This means exposing yourself to a wide range of information and ideas from different sources. You can do this by reading books and articles from other industries, attending events and conferences outside your field, and connecting with people from different backgrounds.

One of the most pragmatic ways of expanding your horizon is to start a side project in another industry that still benefits from the knowledge you have in your existing area of expertise.

You could call that intersectional entrepreneurship.

I was helping a friend with a project in the personal fitness space, and just getting a glimpse into the industry’s best practices was eye-opening as it laid plain all the assumptions I had about consumers in the market. I was way overconfident in terms of technology adoption and literacy. And that learning is something I took back into my writing, making it more accessible to people who become founders without having had a technical career before.

Diversifying your inputs can open up new perspectives and expose you to new opportunities you wouldn’t have otherwise been aware of. It’s all about broadening your mind.

Be conscious of the areas of your life where you may be hindered by your own lack of knowledge, and be ready to put in the hard work and effort to eliminate that lack. The “unknown unknowns” in your life are dangerous. Take the time to step back and reflect on what you could be missing out on —turn them into “known unknowns”— and then invest the energy and effort to move past these blind spots and open up possibilities for yourself.

You can do this by consuming media that intersect with other fields or are created for different industries entirely. I read several newsletters that have very little to do with indie entrepreneurship but are always insightful and instructive. They range from expert pasta chefs’ personal blogs to personal productivity through psychology to scaling enterprise software projects.

Another example here: I subscribe to a newsletter on historical financial systems. For months now, I’ve read about how these complicated systems work, have worked, and how resilient they are to being modernized. I have also understood that friction in banking is a built-in benefit, not a hindrance. While it’s annoying that banks call you up for confirmation or require waiting periods, you only have to look at the many irreversible losses in the crypto world when funds were routed somewhere by mistake. A system with friction might have caught and prevented that. If I were ever to dabble in building a FinTech software business, my priorities would probably be less on friction removal but on finding another way to provide and improve upon what the traditional systems already make possible.

You’ll never know what news from an adjacent field might inspire you to integrate it into your own. An open mind grows your opportunity surface.

Inching Closer to the Dream

Finally, you can increase the size of your opportunity surface by inching closer to your dream. This means taking small steps towards achieving your goals and working towards your long-term vision. Instead of waiting for the perfect opportunity to come along, take action and create small opportunities for yourself — today! Start that side project, launch a small test campaign or reach out to potential collaborators with a small but impactful idea.

Baby steps in the right direction.

This is a part I want to stress: you don’t need to get the maximum results the first time you attempt something. You just have to progress a bit closer in the direction of those goals. Sometimes, going for an adjacent project might give you enough of an in to get to the main goal later. Instead of getting an enterprise customer right away, find out who their distributors and dependencies are and target them with your services. The word might bubble up to the bigger client, creating organic interest over time.

It’s like finding your dream job: you’re better off getting your foot into the door with a different role in the industry than holding out forever for a job you won’t get because you never built the network to make you aware of an opening.

You might feel that you’re not ready. But the fact that you can even take a tiny step towards it means you are ready. As ready as you can be. The thing with “the dream” is that it’s asymptotic: you can always get closer, but you’ll never reach it. The dream is a moving target — and you have to move with it to keep up.

Entrepreneurship will never be easy. But we can make it less hard. luck can be influenced by working on increasing the size of your opportunity surface. By doing things that don’t scale, diversifying your inputs, and inching closer to your dream, you will increase your chances of success.

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I'm a huge fan of Descript for editing audio and video — which I have to do a lot. Used to take me two days, now it takes two hours.
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​MicroConf US is happening from April 16th to April 18th. I'll be there, and I will be speaking — of sorts. You can book your ticket for $100 off using "arvid100" at checkout.
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