Last week, I was asked to write up my “Top 10 bootstrapping actions” for a book on bootstrapping that should be coming out later this year. Bootstrapping must be in the air as Fred just wrote about how he teaches about it in his course at NYU Stern and Jerry just wrote about it for his Inc. Magazine column Forget VC Money, Fund Yourself. I recognize the potential dissonance about VCs writing about bootstrapping (or – “how to create a business without taking money from VCs”) – I know Fred, Jerry, and I all feel strongly that VCs are only a small part of the entrepreneurial / company creation ecosystem and the vast majority of companies that get created never take VC money (my first business raised $10 – we had 10 shares of stock at $1 each – and – when we sold it – each share made a share of Google seem like a penny stock – although we only had 10 of them.)

I spent some time with the author – Marcus Gibson – and felt his questions and probing style were very good. Following is my Top 10 list and commentary I gave him to work with.

1. Figure out how much cash you really have: When someone says to me, “I’m thinking about starting a company” I typically ask them “how much cash do you have.” They usually answer something like “none”, not realizing I am asking them about their personal resources, not the business resources (or investor dollars). I clarify and explain that they are likely going to have to go a period of time with no salary, pay for expenses out of their own pocket, and invest in various things for their new business. I’m not being nosy (and in fact don’t care what their answer is) – I’m trying to make the point that they need to make sure they are cognizant of the potential personal economic toll that starting a business entails. Obviously, some of this is mitigated by an angel or venture investment, but there’s almost always a period of time prior to this investment (and could be forever in the case where no money is ever raised) where the entrepreneur is essentially funding the business, whether it’s through their own lost opportunity cost of not having a job or – more likely – through writing checks or loading up on personal credit card debt to get the business started. It’s critical for a bootstrapper to understand how much financial capacity they actually have.
2. Figure out how much time you really have: The cliche “time is money” applies to starting a company. The amount of time one has to get a business going is often directly linked to the answer of how much cash one has to get a business going. Often, entrepreneurs overestimate how much time they really have, either by only partly dedicating themselves to their new business (e.g. working a full time job and trying to start the business on the side) or setting expectations that the business will be up, running, and generating enough revenue and income to pay full salaries within an unrealistic period of time. In almost all cases, an entrepreneur is going to have to invest substantial time in a startup to get it off the ground. Understanding how much time you have before you run out of cash, energy, spousal patience, or market opportunity is important to think about going into the startup phase.
3. Pick a domain and go deep: If your answer to “What kind of company are you going to start?” is something like “Well, I have a few different ideas…” stop immediately. You should pick one idea in one domain and go extremely deep on this idea. Optimally, it’d be something you already know a lot about so that you’ll be leveraging your personal experience and presumably one of your passions. Hedging your bets by thinking about and playing around with a variety of different ideas is a huge waste of energy – you need all of your focus on the one thing you are going to do. Early in my life as a VC, I was in a meeting where an experienced VC asserted that one of the most important questions for a venture-backed company to answer is “What do you want to be the best in the world at?” I think this question broadly applies to all entrepreneurial endeavors.
4. Surround yourself with experienced people: This is often easier said than done. When I started my first company, I had a very small network which consisted mostly of my father and several of his business friends. Fortunately, I had the advantage of age (or lack thereof) on my side and several of my early clients took me under their wing and acted as mentors for me and my partner. After I sold my first company and shifted my role to be an angel investor in startups, I helped start several companies with young, first time entrepreneurs. I saw first hand how impactful having experienced folks around the first time, inexperienced entrepreneur can be as my new first time entrepreneur friends were perfectly willing to make exactly the same mistakes I had made eight years earlier when I was starting out (hopefully I was able to help them avoid most of them while we made new and exciting mistakes together.)
5. Find angels: This is a corollary to surrounding yourself with experienced people. While angels are typically associated with “angel investors”, they can also be part time advisors that will work for equity to help you get your business off the ground. I’ve found that finding people that are willing to help for equity (and no cash) are surprisingly easy to find. The trick is finding “angels” (vs. devils) – folks that can really help you and are on your team, rather than people who have an agenda other than helping you succeed and are willing to make a buck in the future if you are successful.
6. Figure out who you want to look like in 5 years: In 1990, I was sitting in an Inc. Magazine / YEO Birthing of Giants retreat which, at the time – was by far the best professional development experience I’d ever had. I got to spend four days with 59 other entrepreneurs who were running companies from my size (10 people, $1m in annual revenue) to much larger ($250m in annual revenue). We sat together all day, listening to lectures from MIT and Harvard business school professors, other entrepreneurs, and each other. We partied at night and got to know each other well. One of the recurring themes that came up over the long weekend was to look out into the future. I took away an idea that I continually use – I pretend that it’s five years later and I define what my world / business / life looks like. I then look backward and write the story that got me to this point. When you are starting your new company, use this tool. Figure out where you want to get to. I can guarantee with almost 100% certainty that it won’t play out the way you initially envision, but at least you’ll have a vision for where you want to get to that you can start with and adjust over time.
7. Get customers: Customers can help address almost all the issues that a startup faces. Most importantly, customers generate revenue and cash. But customers also help shape the product, business parameters, validate the ideas, and provide “honest work” for you to do. In the MouseDriver Chronicles, the authors state that business consists of only two things – making and selling. Getting and having customers helps you focus on this. Successful customers will also typically help generate new customers as well as confidence that your business is doing something useful.
8. Learn everything you can about what you are about to do: This is the corollary to “pick a domain and go deep.” Great startup entrepreneurs are intellectually insatiable about the thing they are trying to create. Learn everything you can about your product, market, competitors, and customers. If you are starting your first business, make sure you spend time learning about yourself and your motivation; figure out what is important to you and why. Be relentless about learning how other entrepreneurs do things, especially those that have had both great success and great failures. If you can figure out how to build continuous learning into what you are doing – without it being a rationalization for not succeeding (e.g. I can’t stand the phrase “We had a lot of ‘learning’ from that experience” – it’s both poor English and shallow thinking – don’t “have a lot of learning” – dig down deep and get to the essence of what is going on a talk about that) – you’ll both have a better chance of succeeding while having a lot more fun.
9. Figure out your fallback plan: You might fail. It happens. A lot. Your initial idea might be stupid. Potential customers might not care. Competition might be more significant than you thought. You might do a lousy job of delivering your product or service. Failure can be terminal to a business, or it can merely be a setback. If you’ve thought about a fallback plan, especially if you have limited financial resources, you’ll have a different mode you can shift into planned in advance. Time is always working against you when you start a company – the more you’ve thought through the different scenarios – the greater your chance of ultimately being successful.
10. Figure out what to do if you fail (face your fears before you start):One of my favorite quotes is from Dune – “Fear is the mind killer.” I’ve always believed that fear is one of the most completely useless emotions. “What if I fail” is one of the biggest fears of a startup entrepreneur. Face it – play with it – figure out what happens if you fail. In most cases, failure is not going to be death (although it could be very uncomfortable). Understanding what your fears are and trying to stare them down in advance of actually encountering them will help you enormously in the process of trying to create a new company.