Sink or swim: why bootstrapping will make you a better entrepreneur

Back in 2005, I had a predictable routine.

I’d get up early, leave my apartment in Brooklyn Heights and tote my laptop to the local Starbucks.

After a few hours of work, I’d stroll across the Brooklyn Bridge to the West Village and settle in at another coffee shop.

By mid-afternoon, I was so caffeinated I could barely type. I had to switch to decaf if I was going to make it to my NYU marketing class that evening.

These were the early days of building my company, Jotform. I was so excited about my idea to create drag-and-drop web forms. But, that doesn’t mean it wasn’t challenging — or overwhelming at times.

We often view the past through a nostalgic, soft-focus lens: our first months of college. The hazy thrill of a new love. The tough-but-invigorating months spent building a business or chasing a dream. All the rough parts get smoothed away and we’re usually left with happy memories.

Thirteen years later, I remember those long New York days with great fondness. I’m humbled and grateful that my simple idea grew into a thriving product with 3.2 million users and over 100 employees.

But if you’re in the scrappy, early stages of starting a business — without venture capital or investors — you’re not alone. I know that the struggle is real.

It’s not easy to grow a business without external funding.

You have to swim, or you’ll sink fast. 

You also have to stretch your resources and work efficiently. If you’re in the deep end, without a life jacket, it’s time to get creative.

Here is why I believe bootstrapping will make you a better entrepreneur and how to embrace its challenges:

1. Wear all the hats — until they weigh you down

Maybe you’re a developer, a designer, a product engineer or an artist. If you’re a bootstrapped founder, then you’re also the customer service rep, shipping and receiving department, marketing and PR agency, and HR manager. You do it all.

Juggling the “other stuff” while you’re trying to create an amazing product can be frustrating. It seems like wasted time, and it takes you away from what you love (and are probably best at) doing.

I took that NYU marketing class because I needed to learn how to promote my product. I couldn’t afford to hire anyone.

I can’t say it was the best use of my time, but it did get me excited about the possibilities. I also read all the marketing blogs, books and free resources I could find, in order to stretch my thinking.

Customer service was the same story. For the first six years, I was the only person doing our customer support.

Even after I had hired a full-time designer and a developer, I worked from morning to night answering emails and support calls. Eventually, I knew it was time to invest in a customer service team.

How did I know when to spend the money? 

First, we’ve always had a rule that we only hire someone when we have their entire first-year salary in the bank. That box was checked.

If you have the resources in place, look closely at your time. Founders should be working strategically. You need to plan the next steps and envision bold, creative directions for the business.

You should be solving big problems.

If you’re spending all day sourcing employee computers or installing software and you can afford to delegate, get the help you need. Take off a few of those hats.

2. Be honest about what’s essential

Toddlers can be volatile because they’re learning about wants versus needs. They want all the toys, but they need to share with their siblings. They only want cookies, but they need to eat some fruits and vegetables.

Founders can get distracted, too. You can build an incredible product from your home, instead of renting a pricey office.

Don’t sign a lease until you absolutely have to expand. Use open-source software, if it works for your business. You can always upgrade later.

Learn the skills that will elevate your product and put them to use. Do the PR and the accounting until it’s getting in the way of your success.

Most people don’t like to think about entrepreneurial sacrifices. Yes, startup culture often glorifies the long hours and the 24/7 hustle, but most successful founders make other tradeoffs that you don’t always hear about.

In 2006, I moved from New York back to my native Turkey. I loved the U.S. and I wasn’t necessarily ready to leave, but it was time to get real office space and hire my first employees on a budget.

Returning to Ankara allowed me to keep those costs down. I could move forward without putting my fledgling business in danger. It was a sacrifice I made for the sake of the product.

Many years later, we opened our San Francisco headquarters. It was a full-circle milestone — and a proud moment for me, personally, because it felt like my early choices had been paid off.

3. Remember that perfection takes (too much) time

Ağaç yaş iken eğilir.

Roughly translated, this Turkish proverb means “the tree branch should be bent while it’s young.” It applies to landscaping, parenting — and business.

If you’re bootstrapping, money is probably tight. You have to rely on savings or early-stage earnings to stay afloat. It also means you have to move fast. You can’t afford to work slowly (unless your last name is Rockefeller).

On the bright side, it’s so much easier to shift direction in the early stages of a startup. You can release a product, get real feedback, and adapt to market needs. Like the proverb suggests, your business is still pliable.

But a tall, sturdy tree with long branches and deep roots will resist change. Long-established product features and designs can make it technically challenging to shift direction.

From an emotional perspective, you probably won’t want to change course on a fully built-out product, either. VC-backed founders who spend years on the “ultimate” first release tend to believe more in what they’ve made, versus what customers tell them.

It’s human nature to feel invested when you’ve spent major time and energy on a project. That’s why the lean, fast-moving startup model can actually be an advantage.

When I mentor young founders, I always advise them to release their products as soon as possible. Don’t wait to make it perfect. Get it out there, listen to real users, and keep refining. Not only will your tree still bend, but you’ll avoid missing a big opportunity.

Why? As technology evolves, people naturally develop the same ideas. It happened to me. No one had made simple web forms before 2006 (when I released Jotform), but three competitors emerged in that year alone.

They saw the same market gap and were busy building their products while I was hopping between NYC coffee shops.

So, seize your moment. Share your work as soon as possible. It’s the best way to compete against well-funded startups (and those rare trust-fund entrepreneurs).

4. Keep swimming, on your terms

Bootstrapping isn’t the easy route. It takes dedication, creativity, and confidence.

But despite all the challenges, I still think it’s the best way to build a business.

If you’re struggling and dreaming of a bank account flush with VC cash, consider this your pep talk. Let’s recap all the reasons why you should stay the course:

• A small team (or a business of one) is easier to manage in the early days. You can focus on your product or service, instead of getting distracted with hiring, HR, office build-outs and reporting to nervous investors.
• You can shift and adapt your product based on user feedback. Your tree is still flexible. Make the most of this time and keep refining.
• Wearing all the hats makes you an expert, which is invaluable when your business grows. You appreciate what it takes to do PR, customer support, and marketing, so you’ll know how to replace yourself when that day arrives. In the long run, understanding every corner of the business makes you a better entrepreneur — and a stronger leader.
• You can slowly build an authentic team culture. There’s space to make mistakes and learn as you go.
• Budget constraints can breed creativity. I know it’s easy to say, but it’s still true. You’ll work smarter if you stay focused on the essentials. Look for innovative solutions. Seek the workarounds that prioritize your core offering and your customers.
• You’re in charge. This is the best advantage of all. No one owns you and no one can stop you from spending a week picking olives if that’s what you want to do. You can run your company how you want, when you want, with the people who make you excited to get up every day and go to work.

So, let’s raise a glass to all the bootstrapped founders out there. Whether you’re fired up about the process or you’re feeling defeated today, keep swimming.

Embrace the challenges and use them to build your strength and endurance. Whatever happens, I’m cheering for you.