For the last 9 months I’ve been in training to compete in the inaugural Ironman Lake Tahoe, a 140.6 mile swim, bike and run at 6000+ feet…and as if that wasn’t enough of a challenge, I’ve also been working on my latest business venture, Bonfaire, that officially launched earlier this year.

The combination of the two has caused me to reflect on some parallels between completing an Ironman and starting a new business.

I’ve heard said that “business is a marathon not a sprint”…

…to hell with that, I say it’s an IRONMAN not a marathon!

[contentheading]It Requires Endurance[/contentheading]

First, for us mere mortals, an Ironman triathlon can seem like a never-ending 14-17 hour test of endurance that no amount of training can really prepare you for. Likewise, running a business can seem like a never-ending, monumental test of endurance that no amount of education or work experience can really prepare you for.

[contentheading]It’s Multidisciplinary[/contentheading]

Second, an Ironman requires mastery of multiple physical disciplines, at a high level of endurance: it’s a 2.4 mile swim; followed by a 112 mile bike; finishing with a 26.2 mile marathon. You’ll not get far if you’re a great runner, but can only swim 100 yards. Likewise, a startup requires mastery of multiple disciplines, you might be a great developer, but if you know jack about fundraising or the needs of your market you aren’t going to get very far.

[contentheading]The Game Changes[/contentheading]

Third, an Ironman involves distinct transitions, after you complete the swim you need to strip off your wetsuit, don your cycle shoes, grab your bike and get those legs moving in a completely different way from what worked for swimming. Once you’ve finished the bike you need to dump the cycle gear and get your trainers on, at this point your feet feel like bricks as your leg muscles go from peddling to running. That’s why they say a triathlon is really 5 disciplines not 3! Likewise, a business often goes through transitions where you can’t keep doing what you used to do and still to be successful, no point continuing to swim when it’s time to bike. Unfortunately, in business, transition points are much less obvious.

[contentheading]Time Is The Enemy[/contentheading]

Fourth, time is of the essence. For an Ironman, if the race starts at 7am, you have 2 hours 20 minutes to complete the swim and must be off the bike by 5:30pm and across the finish line by midnight…otherwise it’s game over. Likewise, when starting a business (particularly a venture-funded startup) you better have reached those critical milestones before you run out of cash or you won’t get to continue on to the next stage.

[contentheading]It’s Lonely Out There[/contentheading]

Admittedly, unlike an Ironman, a startup is a team sport, but like an Ironman, as CEO it can sure feel lonely.

For an Ironman surviving to cross the finish line is reward enough; for a startup, the reward is surviving long enough for a finish line to appear.

If you’d like to support my Ironman efforts and donate you can click the button below, the money I raise goes to help those with disabilities continue to lead even more active lives with the aid of prosthetics and adaptive devices that often aren’t covered by medical insurance.

Help me raise $6000 for the Challenged Athletes Foundation

Fear, uncertainty and doubt…you may look at successful people and think “I wish I was like them and didn’t have all this fear, uncertainty and doubt” as you look to start your new venture…here’s the thing, those people have been successful despite having the same fears, uncertainty and doubt as you…not because they have none.

For most of us looking to start a new venture it’s the first time in our professional lives that there hasn’t been someone else that we can put our faith in. Whether that be a manager, a senior leader or a CEO. Hell, even as a co-founder of Kaboodle I was still able to put my faith in my fellow co-founder who came up with the original vision.

As you go it alone, it’s time to put your faith in yourself, your idea and your abilities to make it happen…and whilst it might seem subtle, anyone who’s been through it, I’m sure, will attest to it being a huge shift…employee to founder or even co-founder to founder…and not everyone has what it takes…the question is do you?

And if you do, how do you dance with the fears, the uncertainties and doubts so they don’t control you?

One strategy as you look at getting started is to look for validation along the way. Anyone familiar with Lean Startup methodology might be thinking about minimal viable product and customer discovery…very important, sure. However, there’s the validation of:

[list class=”bullet-minus”][li]Having a co-founder as crazy as you about your idea[/li] [li]Having people willing to put in sweat time on the side of their full time jobs to help you build out a proof of concept[/li] [li]Finding some advisors interested enough in what you are doing to inject their experience[/li] [li]Finding some angel investors or VCs who might be willing to write you a check[/li][/list]

The loneliest and darkest time is when it’s just you and your idea…it’s those that work out a way to build a movement around their idea that reap  the rewards of starting a new venture…and I assure you, they are no different from you.

[div3 class=”quote” class2=”quote-l” class3=”quote-r”]Faith is to believe what we do not see; the reward of this faith is to see what we believe.[/div3]

– Saint Augustine

How true…

As a student of entrepreneurship I love to learn and more recently I’ve been immersing myself in approaches/mindsets for starting technology businesses. There’s the “venture capital” mindset here in Silicon Valley…and then there’s the “business owner” mindset in (what I call) the real world.

[contentheading]Mindset #1 – The BIG Idea[/contentheading]

So strategy one, you’ve got a BIG idea, it’s a potential $1B opportunity, you’re driven to create the next BIG thing, to create a BIG business and make a BIG impact. You want to raise venture capital and shoot for the stars!

Thanks to my Kaboodle experience I have a great reference for the venture capital way of doing things, from starting in a garage, raising angel investment, building a team, raising series A financing and ultimately being acquired. Chances of success…1 in 100, 1 in 1000, maybe 1 in 10000? You either succeed or you do not…it’s boom or bust. Venture capitalists want venture-sized returns in the next 3, 5 or 7 years. They’re not interested in a highly profitable $10M business…even if that cash flow could provide you a great quality of life.

[contentheading]Mindset #2 – The Business Owner[/contentheading]

There’s an interesting counter movement in the technology startup space championed most visibly by the guys at 37Signals in their book ‘REWORK‘. In case you’ve never heard of them, they started as a small web design firm that built a simple online project management tool (Basecamp), to solve a problem they had working with clients, that itself grew into a sizable business.

So strategy two, you’ve got an exciting business idea, it’s a solution to a real pain point that businesses or people will pay for. It might not be a $1B opportunity, but it could well be a highly profitable $10M opportunity.

In the “real-world”, if you’ve got an idea for a $10M, highly profitable business that requires little startup capital and has no fixed costs – well, most business owners would jump at the opportunity. Chances of success, hard to say…is it more likely to build a successful $10M business or a successful $1B business?

37Signals didn’t raise venture capital, they haven’t tried to grow to be the next Facebook, instead they’ve stayed niche, focused on adding value and have built a highly profitable business that I can only assume creates a great cash flow and lifestyle for the founders. They’ve thrived over the last decade through 2 downturns, remained profitable and if you were to compare them to businesses outside of the venture world they’re amazingly successful. I have many friends who are business owners that’d kill to have a business with 3 million customers that pay a monthly subscription with only 15 employees…that’s been around for 10 years!

Yes, we’ve heard the stories of the guy building the next hot mobile game and suddenly hitting it big, this isn’t what I’m talking about, 37Signals isn’t a get-rich-quick story. It’s a story familiar to any business owner, find a pain point, serve your customers and make money – don’t burn it. They just happen to build web applications instead of washing your car wash or dry cleaning your clothes.

[contentheading]Which Are You?[/contentheading]

I’ve met a number of budding entrepreneurs with great ideas that assume they have to go raise funding. The challenge is many of these ideas just don’t strike me as being venture fundable ideas (at least to me). I don’t see the $1B market opportunity. That said, they do seem to be great business ideas that could add value to people’s lives.

With today’s ecosystem making it real easy to build & deploy web/mobile solutions and the Internet making it real easy to reach potential customers I wonder if we’re in a renaissance period for nerds. The small business of the future might just be an Internet or mobile app rather than a McDonald’s franchise!

As I begin looking at starting my next venture I’ve been reflecting on what should I be doing NOW before I start, to significantly increase my chances of success…and I believe there are four things.

If you’re a budding entrepreneur just like me read on…

[contentheading]Who Am I?[/contentheading]

First, decide you are an entrepreneur.

Our identity shapes how we think and the actions we take…if you want to be an entrepreneur the first step is to decide you are an entrepreneur.

[contentheading]Who’s My Team?[/contentheading]

Second, find someone who’s going to be crazy enough to come join you (maybe even a couple of people).

Interestingly, there’s a project called the Startup Genome that is attempting to unlock the secret to what makes startups successful, one of their findings based on a survey of 650 companies is:

[div3 class2=”quote-l” class3=”quote-r”]Solo founders take 3.6x longer to reach scale stage compared to a founding team of 2.[/div3]

If you can’t convince someone else to be as crazy as you, how are you going to convince someone to invest in you and your idea? For some inspiration on ways to start building your team read “Starting a Startup“.

[contentheading]Who Am I Connected To?[/contentheading]

Third, get connected.

The first time to meet a potential investor/advisor is NOT when you actually need their money/advice…not unless you’re being introduced by someone who already knows the both of you well.

Again from the Startup Genome project (regarding this point and the next):

[div3 class2=”quote-l” class3=”quote-r”]Startups that have helpful mentors, track metrics effectively, and learn from startup thought leaders raise 7x more money and have 3.5x better user growth.[/div3]

[contentheading]Who’s Been Successful?[/contentheading]

Fourth, study.

Become a student of startup success and failure stories. Research the latest in business and product development thinking specifically as it relates to innovation and startups.

Personally I really like the work Eric Ries has been doing with The Lean Startup movement and highly recommend his new book “The Lean Startup“, I was fortunate enough to get an early copy.

…and OK, I know I said there were only four, but there’s five really…

[contentheading]Take Action[/contentheading]

Fifth, take baby steps.

At some point you’ve got to commit, it may take you 6 or even 9 months to gestate your idea, identify your team, investors and advisors and bone up on how this startup thing works, but then you have to jump in. The question is now as you look to the future 6 or 9 months away what are the baby steps you must be taking today? What do you have to be doing NOW to create that compelling future.

More from the Startup Genome project:

[div3 class2=”quote-l” class3=”quote-r”]People who work half time raise about 24x less money than founders who go full time. They also have trouble building up the intensity required to drive the user growth needed to validate interest in their product.[/div3]

You will never stop working on these 4 (or 5) things, even once you’ve started your startup, but trust me the time to start working on them is before and not after you’ve quit the day job!