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Patrick Bosek of Jorsek: “Spend more time finding the right customer rather than trying to be right for the first customer”

Spend more time finding the right customer rather than trying to be right for the first customer. Just because you have a product and a target market doesn’t mean you have your target customer completely dialed in. Many markets are very large and that often makes them diverse in their demands of your product. A […]

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Spend more time finding the right customer rather than trying to be right for the first customer.

Just because you have a product and a target market doesn’t mean you have your target customer completely dialed in. Many markets are very large and that often makes them diverse in their demands of your product. A product-first company can be tempted to build all the features and functions that the market demands; in my experience, this is a mistake. It’s a far better idea to sub-segment your market down to just the customers who love your product as it currently exists. This may mean you focus on an industry style niche inside your market, or it may mean that you focus on a set of attributes that are more built around company structure or culture.

This is advice that definitely falls into the “easier said than done” classification and it’s something we still get wrong from time to time, which is OK.


As part of our series called “5 Things I Wish Someone Told Me Before I Began Leading My Company”, I had the pleasure of interviewing Patrick Bosek.

Patrick is Co-Founder and CEO of Jorsek Inc., makers of easyDITA. Since beginning with Jorsek in 2005, Patrick has worked on a wide range of projects all focused on improving authoring, production, and distribution of content. Most recently, his primary focus has been empowering the users of easyDITA and generally advancing the product documentation industry. Patrick is a software industry professional specializing in developing, productizing, and solving problems with product content software. He is a skilled developer, thoughtful manager, and passionate customer advocate.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

My co-founder and I have been working together on structured content systems since we were in college. We got started by writing publishing systems for Judo and then for a local hospital while we were still undergrads. Once we graduated, we decided that we’d like to keep working on this type of technology since we felt it was the future of content. Broadly, we were right, but it took a lot of twists and turns before we found our niche inside the massive industry.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

Roughly, 2010 or so. We’d been working on things related to structured content and publishing for a while, but the way we wanted to approach this space wasn’t lining up with the users we were targeting. Somewhere in this timeframe, we bumped into some people that pointed us toward product and technical content. Once we saw the challenges and direction of this industry, we knew it was a fit for our approach and the technologies we had been working on.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

Yes, plenty of times. We largely bootstrapped the company until late 2019. I’ve only bootstrapped one business, but in speaking with other people who’ve done it, I think my experience isn’t too far outside the norm. Bootstrapping a high-tech company is hard, there’s no way around that. It’s not like opening a bakery (which, to be fair, I assume is also quite difficult), you don’t open your doors with a product ready to sell, and your product is never really done. You have to build your product while you’re selling it. You often have to sell a product you don’t completely have yet, sometimes that means you miss and people get angry with you. And this is doubly hard today because the pace of change is so high.

There were many many nights that I questioned the logic in continuing to push forward. I don’t have a good answer to where I got the drive. Some portion of it is certainly the fact that my partner and I had a vision for how we feel things should work in our industry and we wanted to realize that, but suggesting that it was pure faith in our mission wouldn’t be honest. The truth is most days I kept going because I had made commitments to our customers.

So, how are things going today? How did your grit and resilience lead to your eventual success?

Things are good, great even. We’ve grown substantially. We’ve got a great team. We’ve got great customers. And we’re in a market space that is undergoing a lot of change as organizations are pushed to rethink how they manage their knowledge content.

It’s hard to say exactly how, or if, my/our resilience led to this. There is no doubt that the key players on our team have a ton of grit. The people who have been the foundation of this business are all very high-grit people. I think like many other things in life, the mission selects the missionaries as much as the other way around. We needed resilience and grit to get to where we are, so we found it.

What do you think makes your company stand out? Can you share a story?

Our culture, innovation, and dedication to support. Probably in that order. Our company works really hard to further the mission for our customers. This is built into the DNA and culture of the company. The people who work here are incredible people and together they form a team that punches way above its weight.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘takeaways’ you learned from that?

There is a feature in our software that allows you to filter content based on a predefined audience. This can be done at any level, right down to a single letter, if you choose to do so. That said, just because you can do something, doesn’t mean you should. One of our first customers really wanted the ability to do extreme filtering on their content. In the sales process, I told them that they can filter at any level, it’s entirely up to them on how they set it up. Well, 6 months went by and one of their users had set up a massive number of filtering combinations and was layering them together so that they would be on paragraphs, phrases inside those paragraphs, individual words, and — finally — single letters in those words.

Technically, it worked, but it was a completely indecipherable mess. The customer got angry when it got so complicated that they couldn’t figure it out anymore and insisted that it was our fault (more specifically my fault) because we had told them this worked.

On our first call on this subject, I laughed a bit because I thought they were joking, or maybe teasing, when they pointed the finger at us. It seemed so clearly absurd that they would blame me for how they chose to use our tool in this particular circumstance. That was a mistake, they did not find this situation funny. This whole episode didn’t end particularly well, but it was a good lesson in many ways. The customer isn’t always right, but often they may believe they are, so until you can confirm their point of view, it’s best to assume they don’t believe they’re at fault. Also, it’s a good idea to understand how someone wants to use something before assuring them that it can be used in that way, even if your assurance is technically correct.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

Content marketing is the future of marketing and selling. There are a lot of very convincing stories out there that want to convince young entrepreneurs that if they build a great product, write some blog posts, and pay for a few Google Ads, people will find them and buy it. I’m sure there are cases where this does work, but it’s very far from a universal rule. There is something very appealing about being entirely product-driven, but it’s dangerous. The truth is that you need salespeople, and more importantly, you need salespeople who are going to go make sales happen, not wait for that fancy content marketing to bring them in. This doesn’t mean that content marketing isn’t a major component of a healthy go to market strategy, but it’s not the only tool in the toolbox.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Dedication. Perspective. Judgement.

Dedication is easy. I’ve dedicated the vast majority of my waking hours to this business and its mission. This is essential. It’s completely impossible to build something without dedication. Dedication is also highly socially contagious. As you scale, the amount of effort, no matter your dedication, you can apply is insufficient; you need dedicated people around you. With rare exception, dedicated people only follow and work for leaders who are equally or more dedicated to the cause than they are.

Perspective is probably my saving grace. In almost all cases, I can step back from a situation and recognize that it’s not nearly as bad as it feels. This is what allows me to sleep at night regardless of what happened during the day. Here’s the thing, there have been countless stressful days, setbacks, and seemingly insurmountable challenges over the years with this business, but at the end of the day, I’m still a pretty lucky and privileged guy. All stress is relative, the beauty in that is that with the right perspective, you get to choose what your stress is relative to.

Judgement is the one I probably preach the most. Good judgement is the difference between success and failure in all the challenging things in life. And that is amplified when time is tight and resources are scarce. Knowing where to say yes, where to say no, when to cut your losses, when to push forward, and when to change directions, is everything. You don’t need to be right all — or even most — of the time, just often enough. I think my judgement has continually proven to be good often enough.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

The biggest piece of advice I would give is to stop wearing burnout as a badge of honor. There is a deeply embedded love affair with working “18 hours a day” and complaining about being burnt out. This is dumb. First off, no one works 18 hours a day with any frequency. It’s just not possible. Go get a time tracking app and track the time you’re actually working, it’s nowhere near 18 hours, I promise. So stop selling yourself this story. I’m sure you work hard, but being burnt out is a frame of mind more than anything else. If you walk around all day telling yourself and other people you’re working 18 hours a day, you’re going to believe it. Tell yourself a better story.

But that only goes so far. As I’ve said, starting a company is hard work, and it is a lot of work. Luckily, I think there is a fairly straight-forward formula for dealing with this issue.

If you’re really working too much, as I have at many points, try organizing the things you’re working on by importance. Then, see what happens when you stop doing the last thing on the list. Weigh the negative impact against the personal benefit you receive by recovering that time. If you’re working too much and you can’t even stop performing your lowest priority responsibility, then you need to hire someone. If you’re not making enough money to hire someone, then you need to decide if your business is really viable.

Lastly, a change of jobs is as good as a break. Cut your day in half, focus on one related set of things for the first half and a completely different set of things for the second half. This was a strategy I used for many years. Selling and account work from 9am — 3pm, writing software from 3pm to whenever I decided to quit.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

This is a really tough question because it’s so situational and every CEO is going to have their own style. I can tell you about a few mistakes I’ve made over and over.

The biggest mistake I’ve made is thinking I can do too much and saying yes too often. To some extent, saying yes and figuring it out after the handshake ends is what has pushed us forward. You have to do some of this in the early days of a bootstrapped startup. But once you reach a certain point, you need to become a lot more careful. Larger teams are a lot more reliable, but they’re a lot less agile. It’s much easier to drop everything and focus on a new and important opportunity when you’re just a few people. This is just the nature of scaling communication.

In your experience, which aspect of running a company tends to be most underestimated? Can you explain or give an example?

I think this really depends on your exact situation. I’ll give you an answer in the context of my situation, which is a B2B Enterprise SaaS. Our business needs to be a careful balance of sales led and product-led. Too much emphasis on one creates significant issues. There is so much industry focus on being product-led that we’ve tended to underestimate the level of attention that sales requires.

Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Began Leading My Company”? Please share a story or an example for each.

Before I jump into my “5 things”, I want to remind the audience that all of my advice is from the perspective of B2B Enterprise SaaS. I know very little about B2C or mobile apps, if that’s the type of business you’re running, my advice may not be for you.

Thing #1: Spend more time finding the right customer rather than trying to be right for the first customer.

Just because you have a product and a target market doesn’t mean you have your target customer completely dialed in. Many markets are very large and that often makes them diverse in their demands of your product. A product-first company can be tempted to build all the features and functions that the market demands; in my experience, this is a mistake. It’s a far better idea to sub-segment your market down to just the customers who love your product as it currently exists. This may mean you focus on an industry style niche inside your market, or it may mean that you focus on a set of attributes that are more built around company structure or culture.

This is advice that definitely falls into the “easier said than done” classification and it’s something we still get wrong from time to time, which is OK.

Thing #2: There is more than one business model, the one that is in vogue may not be the one for you.

How do you organize your go-to-market strategy? More investment in sales or marketing? How do you mix services versus product revenue? How do you price either?

You can find very strong opinions on different approaches and models scattered across the internet. I think these opinions are extremely valuable because they provide possible structures you can attempt, but where I think they’re dangerous is that they often position their model as the only model that works today. This last part is dead wrong. You need to evaluate the different levers you can pull in your business as they relate to your business.

Take cold calling as an example. If you listen to many contemporary content marketers, you’d think cold calling is dead. Cold calling is very much not dead. If anything, it might be more effective today than it was 10 years ago because so many people have been convinced to stop doing it. That said, does it work for everyone? No, certainly not, it’s situational. One example of a situation where cold calling can work well is when your target customer has a big problem, but they’re not aware of it. This target customer won’t be looking for your solution because they don’t know there is a better way. One of the best ways to get their attention is to call them up and politely ask for it.

Thing #3: One killer feature beats a dozen good ones.

This is actually strongly related to Thing #1. It’s another way of looking at how you create value. The best products do something that users can’t live without. If your product does something that your customer can’t live without (and can’t easily replicate), they’ll tolerate a lot of other annoyances or gaps. This is often hard to see when you’re up close to it because they may still complain about those other annoyances and gaps, but in the end the killer feature will matter more.

Obviously, this is a spectrum and a killer feature is pretty subjective. I think it’s one of those “you’ll know it when you see it” type things. My strongest advice to you is that when you see it and you know it, seize the moment and aggressively find as many customers as you can who believe it to be their killer feature.

Thing #4: A narrow lane often has fewer cars.

There is a lot to say about this one, but at the very highest level, it’s a statement about the fundamental difference of business today.

When you’re selling a direct sale B2B product, market size is almost never your limiting factor, it’s speed. The more focused you are, the faster you can go. This is for a number of reasons, but one of the biggest ones is the simple fact that no one else will do the one thing you do really well quite as well as you.

If you’re going for VC, you need a credible story about how you can address a really big market (i.e. more than a billion), but as an operator, you can’t sell to even a tiny fraction of that market in the next 3 years. So, understand the greater context, but keep your eyes fixed on something more narrow.

Try this: What is the largest number of new customers you could accept this year?

Different companies will have different answers, but the reality is that most B2B SaaS companies can’t scale infinitely, the Service part of SaaS is real, you need people to take on customers. So, assuming you’re among the SaaS companies that are limited in growth by the number of people you can hire and train to fuel and support that growth, this question makes a big difference. Take your answer and divide your total addressable market, even if you grow at 100% year over year for 5 years, how much of that market have you really captured?

Thing #5: All products are toys.

A few summers ago, my father helped me do some work on my house. I remember him showing up one morning with a new hammer. This hammer had a couple of new little things that his old hammer (and my hammer) didn’t have. It held nails for placing them, it was a little easier to pull nails back out, it was weighted very nicely. He loved it. He told me all about it. A hammer is a tool, but it’s also a toy. All tools are toys. Humans love building things, making things, and working on things. The line between play and work is very thin for those who enjoy the task or, at least, derive satisfaction from completing it.

No matter what kind of product your company produces, it will be used more if people enjoy using it. Not in the way they enjoy playing a game, but in the way they enjoy the feeling of a perfect swing of a hammer. That tiny moment of power is pure serotonin.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Geez. I think I would have had a really easy answer to this 18 months ago. The world has changed so much. I think there needs to be a renaissance of perspective across many areas of society. I think we’ve seen that our current system of society has limitations. I’d love to lead social discourse that allows us to really step back and decide if our current systems and institutions are really producing the outcomes we want as a whole society.

How can our readers further follow you online?

Follow me on Twitter and LinkedIn.

I’ve recently started a podcast of snackable content industry chats in 15ish minute weekly episodes: Content Components

This was very inspiring. Thank you so much for the time you spent with this!

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