15 Lessons on entrepreneurship

Our CMO Weighs in After a Year as a First-Time Entrepreneur

After a year in Silicon Valley, people often ask what it’s like living amidst a hotbed of innovators, entrepreneurs and investors, about some of the most important lessons we’ve learned as a start-up and what’s its like working remotely as a team based bi-coastally (in Silicon Valley and New York), with developers in Germany, France, USA and Sri Lanka.

Wonder no more.

Those long nights of insomnia, searching for the answers to these and more are a thing of the past, as of this blog post. Of course…some people enjoy pondering that sort of thing, in which case: SPOILER ALERT AHEAD. 

Can’t say we didn’t warn you.

15 Lessons on Entrepreneurship

1. People, people, people. Angel investor & Venture Hacksco-founder Naval Ravikant put it best when he said “It’s all about the people, stupid.” That is as true for team dynamics as it is for customer and investor relations. You can have the best job in the world, but if it’s with the wrong people, odds are you won’t last very long. Or you’ll be miserable. Having worked in all sorts of teams of various sizes, disciplines and cultures, it’s undeniable: when you have the right combination of dedicated, competent, talented people, you not only increase your chances of success, but mitigate your risks exponentially.

2. Get out there. Connect. Related to point 1, but important enough to stand on its own. When you have an idea, when you believe in it, when it has been sufficiently developed – tell the world. Why? Because 4 minds are better than 2 are better than 1. That’s when you get new perspectives, field tough questions that you may not have thought of before (which, if you work to address them, will only make you stronger in the long run) and establish new partnerships, customers and contact. Even when you don’t meet contacts that are directly related, more often than not (particularly in the Valley), you’ll meet someone who know someone, be they a friend, a colleague, or a mom’s friend’s brother’s dog’s walker’s uncle. At the very least, you’ll practice your pitch, which brings me to…

3. Evangelize. Practice your pitch, know it backwards, forwards and sideways. Evangelize at every opportunity you get – and you should want to! If you don’t care about your product, if your obvious enthusiasm for your work doesn’t come through, why should anyone else care? Is your service really that useful, then? There have been numerous events and occasions at which we’ve begun to go through our spiel only to be interrupted by recent Civi-Inductees who say, “Wait, I love the concept and want to make sure I have the details right. Let me explain it!” When you can turn strangers into evangelists, that’s a good sign.

4. Be obsessed. Mike Lynch of Autonomy said it best: “Unless you are prepared to be obsessed…you probably won’t be successful.” There’s a saying that the best entrepreneurs are least a little bit crazy, and being in the Valley (and part of a start-up!) we’ve witnessed it firsthand. If at least one person of your co-founding team isn’t thinking about your vision, your company, your product and your goals at any given moment, be it 9am on a Monday morning or 3am on a Saturday night, is this something you are really willing to be committed to through thick and thin?

5. Fortune favors the bold. Forgiveness-over-permission is pretty much a mantra in Silicon Valley, and the motto within the CiviGuard ranks is “Bets off, go for it.” When you are trying to make a difference, evolve beyond traditional conventions and get things done, sometimes you have to bend the rules a little bit. (DISCLAIMER: we said RULES, not LAWS). Some of our most important meetings have occurred this way.

6. Be unconventional, be visionary. Forget about what is accepted, forget about what is the norm and play the “Hypotheticals” game with yourself. What if your best-case scenario happened? What are the craziest product roadmaps you can concoct? What is the most success you could possibly achieve in 4 months, and how can you be on your way today towards that reality? What is the most progress could your industry could achieve in 10 years, and how can you be part of it? When you think about your company, if you truly want to be a disruptor, there is only one way to go about it…and it sure isn’t by following the norm.

7. Be resourceful. There’s more to capital than just cash, and when you are in a start-up, you don’t need to embrace this, you need to live it. When boot-strapping, you quickly learn to trade in alternate currencies – time, social capital, skill-swaps – and even create a few of your own.

8. Be fast, flexible and adaptable. This isn’t just good advice, it’s a survival mechanism. You might have to repackage your product, change your target demographic and even change your business model. A start-up is a highly fluid, fast-changing environment, and if you aren’t willing to change your MO to ride new trends, seek new markets and leverage new partnerships, you’ll at best, miss out on multiple growth avenues, but more likely end up burying your company.

9. Be goal, not process-oriented. “I fight like hell to keep process out of it.”Dean Kamen probably said it best, and this relates back to point #8: sure, you can lay down all the processes and policies you want, but when working in a fluid, shifting environment, these are often out-of-date as soon as they are written. This is particularly true in the beginning, when there is more of a need to get things done, rather than figure out how they are done. There’s often more than one way to get to the end-zone but some routes are more efficient and less resource-intensive than others. Sometimes you need to pull a Nike and Just Do It.

10. It’s a roller coaster, not the Tunnel of Love. A start-up is not a fairytale world, and things will not always go as planned. There will be bumps and even chasms. Every company, even seeming overnight successes, have their war-stories and battle-scars, some resulting from circumstances out of their control, and others resulting from personal decisions. Keep your end-goal in mind, and be prepared to make small sacrifices along the way to achieve this. At the same time, realize that 90% of failures won’t ring the death knell for your company.  Just pick yourself back up, dust yourself off, sharpen your spears and hearken the battle cry.

11. Listen to your Spidey-Sense. If there was ever an excuse to hone ESP-like skills, entrepreneurship is it. Not because we subscribe to tea-leaf reading as a means of doing business, but because business is really code for “understanding people” – and as you interact with more people, you really develop a feel (intuition, if you are good enough) for people’s motives and MOs. Thus, when things go awry, it’s easy to spot at some level, although perhaps not always consciously. It could be as simple as body language, tone of voice or even more subtle than that. The point is, when that tingly feeling kicks in, do a double-take and reassess.

12. Have a contingency plan. Hope for the best, prepare for the worst. This is almost an extension of points #6 and 8. Play the ‘what-if’ game and ask what is the worst that could happen? That’s a long list, but at the same time, most of what could be deemed ‘worst-case scenario,’ isn’t as bad as you think. And for the stuff that actually is - better to think of it now and develop a Plan B…but be ready to adapt even that plan should the need arise.

13. Communicate. People often ask us how we manage to work as a bi-coastal team with developers scattered across the globe. In a word: communication. In this day and age, between e-mail, SMS, voicemail, phone, Skype, conference calls, g-chat, Facebook and Twitter, we are extremely well-connected to one another, and interact over multiple channels. Besides, as a team, we get along better than most, and spend a little too much time laughing and less working when we are in the same physical location – so it’s probably best that we don’t share an office.

14. Execution »> Inspiration. Every single time. Everyone has ideas. What defines an entrepreneur as a change agent is their willingness to walk through walls to turn a pile of mind-stuff into a real-world solution. And that’s where execution and effort come in. The best ideas will fail without proper, pain-staking, flawless execution. Being fast and flexible is not an excuse to skimp on the details.

And finally…

15. Love what you do. Don’t do it if you aren’t passionate. Period.

- SP