Startup Lessons Learned

By Ryan Allis

Here are thirty of the most important startup lessons I learned from 2002-2012 while building iContact.

1. Don’t get stuck in analysis paralysis. Take action now.

Sometimes you’re not going to see all the way to your end destination when you start, but just take the very first steps and the world will open up with new people, new resources, and new opportunities that enable you to achieve more than you can even fathom today.

2. It’s up to you to get out there and do it, to take the initiative.

No one else is going to do it if you don’t. It’s your job to take chances and make things happen.

3. Investors don’t invest in systems that go home at night.

They invest in businesses that have systems and processes that can run even without the main entrepreneur having to be there.

4. Don’t be afraid of failure.

Most people are afraid to fail. They worry constantly about not living up to expectations, about making mistakes, and about trying something new. Because of this, most people never get started on the path toward reaching their goals and their full human potential. In order to become a successful entrepreneur, you’ll have to pay your dues and fail a few times. You’ll learn lessons, and only then will you be able to come through a winner. While you don’t have to take wild chances, you do have to take some risks. And most importantly, you have to get started quickly.

5. Recognition and praise are often bigger motivators than monetary compensation.

Never forget this as you work with your team.

6. Always communicate frequently and openly with everyone, including customers and stakeholders, during negative events.

The worst thing you can do during a negative press event or downtime is be silent.

7. Once you have 80% of the information necessary to make a decision, make the call.

You will be right more often by acting quickly and learning and incrementally improving than by waiting to make the decision until all the information is available. By increasing the frequency of decision-making, you will be able to achieve much more than by simply waiting longer.

8. When things are going well, it’s the right time to prepare for when things won’t be going well.

When you don’t need money, get a credit line. When things are growing at 100% a year, think about what your strategy would be if a competitor were to come into your industry and make your product for free.

9. Building a business is sort of like moving something heavy. It takes time to get the momentum going, but once you do, that momentum can begin to take over and things can start moving even more quickly.

Jim Collins, in Good to Great, calls this “the flywheel effect.” He compares a company to a heavy wheel, and explains, “Your job is to get that flywheel to move as fast as possible, because momentum—mass times velocity—is what will generate superior economic results over time.”

10. Part of the CEO’s job is to find and hire people who can do their roles much better than the CEO could.

When you hire someone, make sure they can do their job at least twice as well as you could.

11. Build consensus about strategy and direction with a small core of your team, and then share widely.

It’s important to choose the right small team to create strategy, at the same time taking in feedback from a large group of people by having automated systems and processes that get input from customers and the frontline all the way up to the senior management team. Once you get consensus, share the strategy with your whole company.

12. When you see someone doing a good job, tell them right then and there.

If you can get into the practice of writing just one handwritten note a day that you can give to one of your team members, people will treasure those notes and you’ll be able to achieve much more and people will love working with you.

13. There is great power in deadlines. Create some.

A deadline is simply a time at some point in the future at which you want something to happen and then there will be some positive consequences if it does happen and some negative consequences if it doesn’t. Deadlines, in reality, are almost always artificial, but a good leader knows how to use deadlines to drive focus on a team. Also, after a key deadline is passed and a key milestone is achieved, giving the team a little bit of time to refresh and rejuvenate is a key part of optimal productivity.

14. To create a great organization, you must build a system to cultivate greatness in leadership potential in others.

You should be investing in your brightest employees, and in their potential to someday take leadership roles within your organization and to innovate and create for the future.

15. Give immediate and specific feedback more often.

This applies particularly to things that you want to be improved. You want to give someone the ability to become great at whatever they do and mentor them along the way.

16. Make sure your incentive structure incentivizes the right goals and the right behavior.

This goes for both your monetary and compensation incentive structure, as well as your intrinsic feedback mechanisms. Take the recent example of the 2012 Olympic badminton teams from China and Korea who purposefully tried to lose because there was an incentive structure from the people who created that game that if they lost, they would actually be advantaged in the next round. Good leaders ensure that incentive systems incent the right behavior—the behavior that leads to customer value creation.

17. Once you get past about 20 employees, conduct annual online 360-degree reviews.

You want to start conducting performance reviews that are written and documented, ideally on an online automated system that includes 360 feedback. 360 feedback simply means that every person within an organization—your supervisor and peers as well as people who directly work for you (your direct reports)—can give feedback on your leadership style, your managerial style, your performance, and your productivity. Often the best feedback you can get is feedback from those who work for you. Yet, for some reason, most performance reviews come from a superior to a subordinate. Often subordinates can give the most valuable feedback to their superior.

18. Have all team members share their personal goals and dreams with their teammates.

It’s important that team members share their goals and dreams not only with the leader but with all of their fellow team members. Once there is a holistic understanding of someone’s true motivations and what drives them, they can often work much better in a team and you can create a managerial structure that aligns what they want to do with their life with the goals that you have for the company.

19. When you get to about 50 employees, hire a chief operating officer.

If you’re going to do a good job as a leader with this many employees, you will need a good COO who can be your operational execution partner.

20. Entrepreneurship is doing something others won’t for about ten years so that you can do what others can’t for the rest of your life.

Entrepreneurship is an investment in your future, in your family’s future, and in your ability to leverage your time and assets to create organizational structures that make a difference in the world. It is something that’s not right for many people. But if entrepreneurship is for you, it can be extremely rewarding and enable you to do things that many people are unable to do. Entrepreneurship is a special field, but if you can be part of it, it can be very exciting.

21. Entrepreneurship is about passion, following a dream, and changing the world, with plenty of craziness along the way.

Dare to think big, and take risks. “Dream no small dreams” as Goethe said, “for they have no power to move the hearts of men.”

22. Becoming a successful entrepreneur is not easy. It’s not for everybody, but if it’s for you, it can be rewarding.

To succeed as an entrepreneur, you must have persistence, dedication, tenacity, and the ability to deal with adversity. If you can have the ability to get through this adversity by being deeply passionate about your mission, great things can be achieved.

23. You may not be able to do everything at once and you need to take a long-run approach.

While companies like Instagram might have sold at 13 employees for $700M to Facebook, it often takes decades to build a company to have created enough value in the world to be worth a billion dollars. But that’s okay, because even if it took 20 years or 30 years to build a company to a billion dollars, you’ve still accomplished something that very, very few people ever accomplish.

24. Play life and play business like a long-term game.

Be good to everyone, respect everyone, treat everyone with kindness and fairness and karma will come back around to benefit you for the better.

25. If you presently today don’t have the financial resources, the experience, or even a good business idea, intern or get a job at a company you are passionate about and start learning.

Particularly if you are a younger or a first-time aspiring entrepreneur, don’t wait for inspiration or for an unexpected windfall. The most important thing you can do is to start getting experience and building your network.

26. Always focus on building quality, giving, and caring authentic relationships with good, caring, quality, authentic people.

At the end of the day, the people in your life end up enabling you to do things (or to not do things) that can allow you to make a difference.

27. Take a proactive role in your personal planning and your business planning with goal setting.

And be sure to regularly evaluate your results personally and professionally.

28. Many people are afraid to ask for help from others, but if you ask for help, people are often willing to help.

Just ask genuinely and find a way in which you can give back to them as well as them giving to you. Build relationships for the long-term, not for the individual transaction.

29. Get experience however you can. 

Build your network, have confidence, and be in it to help others to win and to make a difference. Regardless of what you’re doing, make sure you’re constantly learning and working with people from whom you can learn.

30. If and when you do succeed, give back.

There are many brothers and sisters in our world who have not been as fortunate as we’ve been.