17 Startup Lessons for the Holidays

From a Portland, Maine startup that just raised $745K

1. Ideas are cheap — you need to build something.
2. Think big markets — do not think in the context of Maine, but rather the United States and globally. Regardless, you will constantly be told the market isn’t big enough — until you provide it.
3. Quit your day job — especially if there is early momentum.
4. Find a co-founder. Investors like 2–3 co-founders, not individuals. You also need one who balances your own strengths and weakness — you will help each other to keep on moving forward during all the low moments.
5. Don’t use your own money. But if you do, be sure to draft a promissory note and use the loan leverage preferred shares on your first raise.
6. Bootstrap as long as you can and focus on revenue. Maine forces this issue and there is nothing like real revenue vs. investor money.
7. Hire a good lawyer, and not one in Maine. No disrespect to the local firms but you are laying the foundation for all future deals so you need experience and perspective. We use Goodwin Procter in Boston.
8. Complete Maine Center for Entrepreneurial Development ’s Top Gun program — they are the best supports of Maine startups. But think seriously about doing a real accelerator program — in particular TechStars, and if you’re uber-confident, Y Combinator. Regardless, enroll in Capital Network and attend their workshops.
9. Leverage the Boston startup ecosystem — it’s only an hour and fifty-one minutes away from Portland. However if you have a customer mobile product, begin to invest time and energy developing in-roads into the Silicon Valley and New York City — Boston simply isn’t consumer mobile friendly.
10. Get used to people saying “no”. You have to develop a thick skin quickly and realize that it’s hardly ever personal.
11. Don’t be afraid to walk away from a term sheet.
12. Leverage Maine Technology Institute grants, but be careful of their development loans — many investors don’t like loans. Don’t bother with their equity investment — they require the option to convert preferred shares into common — not startup friendly at all.
13. Leverage Maine Venture Fund, but their terms are not designed for early stage startups. They require a layer of bureaucracy which is hard to justify given their average investment amount and the typically structure of an early stage startup.
14. Leverage Maine Angels, but set a minimum investment amount and stick to it. Like with many Angels groups, you need to be careful not to have too many cooks in the kitchen.
15. Move to close as soon as possible, otherwise people get cold feet.
16. Build a support network of other founders — ideally ones who are slightly ahead of your growth curve. You need to network and reference check potential investors and compare deals. And do it over good beer with a low ABV — so you can actually remember all the advice.
17. Building a startup sucks. There are constant highs and lows — and very little in between. Your abilities will be questioned constantly. Your confidence will take a beating each and everyday. You have be sure it’s in your DNA.

BONUS: Your partner/spouse is your unwritten co-founder. They feel your highs and lows — and all the stress that goes along with it. Never stop appreciating them and thanking them enough.

This was the basis of a talk I gave at Portland, Maine’s PubHub gathering on Dec 2, 2015. I am the CEO and Co-Founder of Chimani. Chimani develops mobile destination guides for national parks and other outdoor destinations. To-date, we have over 850,000 downloads, 200k users, and 20 individual destination guide apps. We are an exclusive launch partner for Google’s new app streaming/indexing technology and recently closed a $745K Series A round of investment funding.