Great results never come easy, right?

Most ideas are great ideas until proven otherwise.

Who is more likely to produce long-term shareholder value — the entrepreneur who raises too much investment capital, or the entrepreneur who funds growth through profits alone?

First time entrepreneurs often have skewed visions of “how it all works”. Their perceptions are often shaped by the numerous successes that get touted about the media, rather than by the 1000-fold number of failures. It makes the “accidental success” of YouTube appear reachable, or at least “just as likely” as any other startup.

One of the things that entrepreneurs usually believe is that once they have an idea, they need investment — that’s just how it works, right? Once they start to talk to investors though, as well as advisors and other folks in the startup community, the questions usually come up … is this a lifestyle business or a “swing for the fences” big market opportunity? A “lifestyle business” is one which you intend to keep running for a decade or two — like my Dad’s optometry practice, for instance, or my brother’s event audio/visual recording business — typically an owner-managed business in which the profits are used solely to support the ongoing lifestyle of the proprietor.

Then there are the “swing for the fences” big market opportunities. These are the startups with big goals, where the entrepreneurs focus on a market opportunity >$100M. To get there, most companies on this track sell ownership in their company at some stage of their business to raise the capital necessary to build their company. Some companies even raise huge amounts of venture capital, at a hefty dilution mind you, before they even arguably HAVE a business. (Twitter comes to mind …) Investors are compelled by visions of a healthy return on their investment, and in the latter case also by extremely savvy entrepreneurs.

For whatever reason, I’m NOT a “lifestyle business” kinda guy. I’m only interested in building a company with a compelling market value and resulting shareholder ROI, but as a founder I’m ALSO uninterested in immediate dilution down to single digit % ownership. I want as much equity in the company as possible.

I learned long ago that the best way to build personal wealth and shareholder value is through “bootstrapping”. Bootstrapping is the art of building companies with very little outside capital/investment. I’m proud of my bootstrapping skills actually, which I’ve developed over four startups now, yet I’ve also realized that outside capital is also essential to developing/realizing a substantial market opportunity.

The reality is that there is a middle ground. Bootstrapping your way 100% to IPO, while honorable, is very difficult and uncommon. If the market opportunity is truly there, being under-capitalized will usually result in missing the market window of opportunity. Conversely, raising too much capital too early rarely results in long-term shareholder value. In other words, given a large market opportunity — a startup that raises too much investment capital is just as likely to fail (to generate shareholder value) as a startup that doesn’t take any investment capital.

I’ve been building Others Online based on what I thought to be an appropriate balance of equity financing and bootstrapping (”sweat equity” financing). Unfortunately we’re still not profitable and thus reliant on investment capital at a time when the market opportunity is large and we’re landing large customers, but market conditions are unstable and investment capital has dried up. And the other day I was talking to one of my investors, who literally wrote the book on bootstrapping, about our status as a company. He insisted that there “has to be a way” to generate more cash from our pipeline immediately. The only way I can see to do that is to shift our business model in the short-term, and I worry that doing so may negatively impact our ability to achieve the “big market opportunity”.

I keep thinking about this. Is it possible to “swing for the fences” (big market opportunity) at the same time as focusing on 1st base (getting to cash flow breakeven)? Or are the two incompatible? I suppose it depends on the market opportunity, but I’d argue most high-value windows of opportunity in the market are open for a limited period of time. Rarely do you not have competition eyeballing the same opportunity, and sufficient funding is generally a prerequisite to nailing these windows of opportunity.

Market leadership positions are always attained as a result of execution. Financing is not execution. However, financing provides the means to develop the necessary components to execution: team, timing, marketing, and product development. Since paths to success are rarely a straight line, financing also helps recovery from bad decisions (on any of the above). Under-capitalized companies are therefore at greater risk. That said, bootstrapping is also essential. It teaches you to make your mistakes quickly and therefore least costly. Bootstrapping is good execution.

2009 is going to be a difficult time for companies who are “swinging for the fences” but aren’t financed for the next 12-18 months.

After a fun-filled, beer-fueled, internet-disabled afternoon topped off with thai food and a test-drive of Danielle’s techkaraoke concept, I put together the following Stephen Colbert-style takeaways from Seattle Startup Weekend part Deux. Hats off to the event organizers for gathering such a committed and talented group of people for a marathon of a weekend.

A fascinating new study posted today indicates that successful serial entrepreneurs have a 50% greater chance of success in subsequent start-ups than either first time entrepreneurs or those whose first venture failed. These individuals were also more readily able to raise venture capital funding and did so under less onerous terms than first-timers.

While on the face of it, Professors Paul Gompers and Josh Lerner are delivering sobering news to first time entrepreneurs, there is a silver lining. The pair outline strategies for newly minted ventures to increase their chances of success by partnering with previously successful founders. Successful entrepreneurs demonstrated particular skill in the areas of market timing and effective positioning of the start-up as a

A while back, when I was working on a business plan for a potential startup, I met up with someone who was also working on a business plan. He was a marketing guy, with limited technology knowledge, so it seemed that we could help each other. His business plan was gorgeous and read well, and it had all the right revenue projections and graphs. Now I’m no slouch as a writer, but mine was dreadful. My plan had accurate descriptions and diagrams of the architecture of the system that I planned to build, and I had a working prototype to go with it. And his plan? He also had some architecture diagrams, but they were basically fiction. I pointed that out to him, but he said it didn’t matter — they were just placeholders and investors wouldn’t care. Guess which company got funding?

I’m not saying that technology people like myself are dismissed entirely, but it’s certainly a much easier road for people with a business background.

So, I was really pleased to hear about the details of the Northwest Entrepreneurs’ Network’s First Look Forum (FLF) earlier this week. The FLF replaces the annual Early Stage Investment Forum (ESIF) that NWEN used to run, with some big differences, the biggest one being that it’s not an investment forum. NWEN properly recognized that there are already plenty of investment forums in the area, but there was very little for the stage before that. And they recognized that early stage entrepreneurs need more than money — they need help. The forum is designed to:

• Recognize early stage companies that show promise and could benefit from the process.
• Help the companies to take their idea and make it presentable, through intensive, personal coaching.
• Provide presenting companies an audience of qualified angel investors that they can present to and network with.
• Provide those angel investors with interesting opportunities that they probably haven’t heard about before.

• What’s the Market and Opportunity?
• What differentiates the concept from others?
• How can the business scale?
• What traction do you have so far?
• Who are you? What’s your experience?

Tags: first look forum, NWEN events
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