Paddleboarding And Business: A Tale Of Sheer Willpower And Perseverance

If you have an idea and want to create something great, don’t fear falling off your board.

Combine surfing with kayaking and you’ve got stand up paddleboarding (SUP). And it is the fastest-growing water sport in the world. Yet, paddleboarding is like many things in life. It’s hard.

The first time I tried to stand up on a board was in a lagoon in north San Diego county. My friend Keith knew of a place where you could rent a paddleboard in a protected area, where the water was mostly flat. 
It took me about 2 hours before I could stand. When I did, I would stand for about 5 seconds, and then down I’d go. 

Again and again, until my quads burned and my frustration level drove me to the brink of giving up.

When we found ourselves on the shallow side of the lagoon, I fell a couple times into knee-deep, sticky, black mud. I wanted to throw in the proverbial towel, but the wind had blown us a mile away from the paddleboard rental place, leaving me no option.

I swore the next time I’d do better. And I did – after another couple hours, I could stand on a paddleboard for all of 10 seconds.

The next time, I made it to 30 seconds, and then, all of sudden, my body learned how to stand on a paddle board. Total time elapsed: 5 hours.

It may have taken me a bit longer to gain the skill and confidence to be able to call myself a paddleboarder, but perseverance paid off.


When perseverance pays off

That experience taught me an important lesson, one that I have learned again and again as an entrepreneur. Our own dedication to a goal is the one thing we can control. Our willpower is the only thing that really stands between us and accomplishing anything.


Photo: © puhhha, YFS Magazine
Photo: © puhhha, YFS Magazine


Starting a business is a lot like learning to paddleboard. Looking back, there were a lot of obvious parallels when I started my first company, CoolerEmail, 15 years ago.

I was consulting and working on building software that made it easy for people to design, send, and track email newsletters. It took 3 years before I could stop consulting and focus entirely on my business. In that time, I fell off “my board” a lot.

As it turns out building a business from scratch is a lot of work. There were a lot of things I didn’t know about managing servers, building software, working with vendors, finding customers, marketing, sales, processing payments, accounting, and the list goes on.



Having an MBA was a start, but the degree only gave me about 10% of what I needed to know. 

After CoolerEmail took off, it was smooth sailing. Much like paddleboarding on nice, flat water, there wasn’t much that could go wrong.

We were first-movers in a new industry. We hired some people to run the business and I traveled the world. This was the paddleboarding equivalent of thinking you could just close your eyes and surf big waves like big-wave surfer Laird Hamilton. You can’t.

When I fell off my board, I fell hard.

The lagoon wasn’t calm, flat water any more. There were sharks in the water, winds and waves of changing markets, and threats from every angle. In thinking I could run a business in absentia, I had let the company and everyone in it down.

Getting back “on the board” was hard and nearly bankrupted me. There were disagreements with my business partner, clients leaving us because our software was no longer as user-friendly as our well-funded competition, and key employees leaving for greener pastures.

I had to act quickly, but I couldn’t make a misstep and react by moving the company in the wrong direction. I spent a couple weeks determining my next course of action. What now?


Getting back ‘on the board’ in turbulent waters

Every business has to consider what value it can bring to its clients.

We knew we could send out emails, but that was becoming a commodity. There are hundreds of email marketing companies on the market. Prices were going down. More people were sending spam. We were going to be marginalized like all of our competitors if we didn’t do something different.

In talking to our clients, initially, one of the things I heard over and over again was about getting email marketing data into other software platforms.

Most email marketing platforms have some nice looking templates that will render well on desktop and mobile devices. Most can tell you when people are opening and clicking on links in emails you send. But the question is what does it all mean?

Does a high read rate indicate anything to your marketing team? Does it impact sales at all? 

Answering these questions of meaning, I saw two potential paths in front of me.


  1. Be an email marketing company, focus all of our energy on that and build integrations with other software that could help someone draw conclusions from the email marketing data collected

  2. Build a platform that helps businesses bring marketing data together with the rest of their operations


Each of these paths had their own challenges. The first plan was much like a long-distance paddleboard race over flat water. The challenge is one of finding partners and keeping the integrations with those partners up-to-date as they continually change and upgrade. It’s not really innovative, but you can build a business around it. You can make a long-distance paddleboard marathon a challenge. A majority of our competitors in the email marketing industry chose this path.

Instead I chose #2. 
Doing something differently from the rest of your industry triggered a lot of interesting responses from people. I presented my new idea, (that which would lead to forming GreenRope a year later) to a room full of industry experts in the summer of 2010. The idea was to get feedback from 100 people who could point me in the “right” direction.

I gave my talk, explaining my vision of creating a unified platform where you could manage marketing, sales, operations, and customer service all in one software. In front of over 100 people, I got absolutely skewered.


“There’s no way you can compete with industry leaders in each of those areas.”

“You’re too small to be able to pull that off.”

“You’re an email marketing company – why change what you’re good at?” 
and my favorite 

“You’re headed for epic disaster!”


This whole experience happened a couple years before I had ever stepped on a paddleboard. Looking back, it was like trying to stand up on your paddleboard, after falling, and having someone tell you you’re doing it all wrong.

And for a split second, I almost believed them.

But then I remembered that the world is full of people who believe in doing things the way they have always been done. For every “You can’t do this!” I realized I was actually hearing “I can’t do this!”

All this “advice” came from people who were too afraid to try something that would change the way they do business.


‘You’re heading for epic disaster’ they said

The path I chose (#2) was like leaving the calm waters of a lagoon and paddling out onto the ocean with your paddleboard. You see waves crashing out there, and you are guaranteed to fall off your board again, but when you see someone out there surfing, you are filled with the inspiration of someone doing something incredible and inspiring.


Photo: © upslim, YFS Magazine
Photo: © upslim, YFS Magazine

One of my personal heroes is Elon Musk. He is the Laird Hamilton of business, truly an icon and visionary, doing things no one thinks possible. He has heard over and over again how something is not possible, and he has proven over and over again that willpower can overcome the impossible. He has said, “Being an entrepreneur is like eating glass and staring into the abyss of death.”

There’s no doubt it’s hard and scary, but you can overcome those fears and build something great if you put your mind to it.


Regaining your balance after many falls

Along the way, I have learned a lot from peers and thought leaders. Guidance from friends and colleagues have helped me see things in a different light, and they have given me emotional support when times have been tough.

Criticism is sometimes hard to swallow and requires a combination of humility and critical thinking.

Sometimes friends are right and they say things that are hard to hear. Sometimes they are wrong. A good friend will recognize that when you choose a path different from their advice that it’s okay. 

The same goes with paddleboarding.

When you fall off your board, miss a good wave, or have run-ins with the often aggressive non-aloha attitude of surfers in southern California, it’s good to know your friends have your back.

I’ve been fortunate to have such incredible friends, and the team behind GreenRope is genuinely 100% good people, who really care about what they do every day.

 In building GreenRope, I have fallen off my paddleboard many times. Mistakes are part of business.

When you’re doing something no one has done before, you’re bound to do something wrong. I’ve had my fair share of “falls” including:


  • Having a developer walk off with $20k in pay without having written any usable software.

  • Having a customer service representative fraudulently report hours (twice).

  • Releasing software that had a bug in it (a few times).

  • Spending money on PR agencies that did nothing for us (several times).

  • Hiring SEO/PPC companies who dropped our lead flow to 10% of what it was prior.

  • Going to a conference and presenting to an audience of 5 people.

  • Donating GreenRope (and my own hours) to help a non-profit use our software only to have one of their managers insult my ability to “sell” to them.


You’ll need resilience and perseverance

Every time you fall off your board, you learn something. You never want to learn the same lesson twice, but sometimes it happens. As long as you get back up on the board, you keep getting better.
 Five years later, I can surf.

GreenRope is stable, growing, and while I can’t guarantee we won’t make any more mistakes, I do know we have built a solid company, with powerful, reliable software. We did it without venture capital, and without a board of directors.



Our team can solve just about any problem, and we compete against companies hundreds of times our size – and win. Although we are not “done” (you should see our to-do list), we have accomplished what we set out to do.

We have built a platform that does what so many called impossible. GreenRope combines sales, marketing, customer service, and operations into a single platform. We aren’t everything to everyone, but we are continually improving, listening to our clients and adapting to the market.

If you have an idea and want to create something great, don’t fear falling off your board. There’s no shame in taking the established path and working harder than everyone else. There’s more risk with going off the beaten path, and there’s no shame in failing again and again. Act with integrity, focus your will, and persevere, and you will create something great.


This article has been edited and condensed.

Lars Helgesson is the CEO and Founder of GreenRope, a CRM and marketing automation platform. He is an entrepreneur, a vet, and an avid adventurer. He builds software to make the lives of entrepreneurs easier. Lars wants to change the way people do business to inspire better customer experiences.
 Connect with @greenrope
 on Twitter.


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