Entrepreneurs are commonly described as: competitive, evangelizing, risk taking, nimble, scrappy, and visionary. However, there is a broader skillset and mindset that entrepreneurs require to be successful.
I'm going to share eight mistakes entrepreneurs make that aren't often talked about publicly. My hope is that I can help you to avoid at least some of the landmines and painful lessons along the way as you build your company.
1. Thinking you can do it all on your own.
Instead: Remember that it takes a village to build a startup.
Continually build a strong ecosystem to support your company, ahead of the curve of where you'll need to most deeply engage it. Enroll as many people as possible in the ecosystem to work for you. Having employees, customers, advisers, investors, and other entrepreneurs sharing your company's core message, raising awareness about your value proposition, and creating general goodwill can help to power you and your company through the ups and downs of startup life.
As hockey superstar Wayne Gretzky says: "Hockey is a unique sport in the sense that you need each and every [person] helping each other and pulling in the same direction to be successful." If you properly align your team and ecosystem, they will help to pull in the same direction towards success for your company.
2. Allowing team or board dysfunction to fester.
Instead: Address signs of dissonance immediately.
The quickest way to blow your company up is to allow team or board dysfunction to linger. The more your company grows, the more you become a manager of people, and you need to be fully aware of and address any people issues before they become a huge distraction, with potentially dramatic, negative consequences on revenue and/or product growth. Having a strong HR executive in place as your company scales can provide a lot of leverage here as well.
3. Hesitating to fire team members who aren't a fit.
Instead: Make tough calls when you need to, and follow through on them quickly.
Accept that not everyone on your team will grow with your company.
This is an area that I have seen almost every entrepreneur struggle with. Providing constructive feedback to an employee who is struggling is of course important. However, the reality is that not all employees, executives included, will be capable of growing with the company as it scales. This can be particularly hard when the employee in question has been very loyal and worked hard--even made personal sacrifices--for you and your company.
In this hyper-competitive world we live in, you do not have the grace of multiple months and years to hope and pray that person will somehow figure it out. Your company and you will suffer if you don't move or replace talent that isn't executing at the level required. (If the employee isn't a strong cultural fit, that is even more reason to move him or her along to find success in a more suitable environment.)
Build and maintain a high caliber team.
Maintain a high bar of having "A" caliber executives in the key functional areas of your company. Don't be afraid to hire people better than you--you can't be an expert at everything. The saying is definitely true that, "A players hire A players, and B players hire C players." Making a poor hiring choice, especially at the managerial or executive level, can create a massive drag on both the culture and growth of your entire company.
You should be hiring at a skill level that will scale with the company for at least the next couple of years.
Making the right decision pays off--often for both parties.
Much relief and increased productivity results from making the right decision and acting on it as soon as possible when an employee isn't growing with the company. And that's often true on both sides, interestingly, as employees often know when they aren't meeting the bar.
One of my entrepreneurs, who had to fire an executive and bring on a new COO, said: "That was one of the hardest things I've done, but it has made a huge difference on my bandwidth and the company's trajectory." And the executive who was fired is also in a situation that suits him much better now.
4. Being afraid to admit that you don't know it all.
Instead: Proactively and continually learn.
We say that our best entrepreneurs "suck the knowledge out of our brains." They take all relevant data from customers, the market, advisers, employees, and investors, synthesize it, and then make the best decisions they can based on that data.
It is OK to not know it all as an entrepreneur. Learn from others' experiences. Make mistakes and learn from them. Continually learn from an executive coach or from workshops in sales, negotiation, leadership, problem solving, and relationship management. Leveraging other resources to learn from is not a sign of weakness but of smarts and strength.
5. Letting ego get in the way of being a strong leader.
Instead: Leverage "high awareness confidence" (not arrogance) and empathy.
There is a fine line between confidence and arrogance. It is important to be confident as an entrepreneur, but arrogance can get in the way of key leadership traits such as listening and understanding, being respectful and earning respect, thoughtfully addressing important issues, and creatively solving problems.
Great power comes from truly stepping into the other person's shoes--whether it be employees, customers, partners, or investors--to understand where they are coming from and build a bridge to a solution with them.
6. Burning cycles on things that don't matter.
Instead: Ruthlessly prioritize the things that matter most.
Meet your commitments, be responsible and accountable, and expect the same from others, but always keep your key priorities in mind and say no to non-priorities. I flew to SxSW in Austin for a work dinner one Saturday evening, flew back home early the next morning to spend Sunday with my family, then flew back to SxSW for another work dinner Monday evening. It is important to compromise for true work priorities, but don't let non-priorities (especially other people's emergencies that aren't your emergencies) creep in, in order to start winning the ongoing juggle of trade-offs.
Our Type A-ness tends to fight the notion of ignoring non-priorities (e.g., letting non-priority email go unanswered), but your life (both work and personal) will eventually implode if you don't start to ruthlessly prioritize what matters most to you.
7. Burning out.
Instead: Unplug and get inspired.
Some pretty high level people in the technology world have openly burned out recently (e.g., Brad Feld and Robert Scoble). This isn't uncommon among entrepreneurs and investors who regularly burn the midnight oil, but many just don't talk about it.
Schedule breaks and vacations. Recharge. Pulling your head out of the weeds on a regular basis will help you to get a better perspective, solve problems more effectively, be more creative, and worry less. It will also help you to be healthier and to avoid hitting a wall. Early in my venture career, I got some great advice: "Sometimes you have to slow down to speed up." How true.
8. Underestimating how challenging it can be to start and scale a company.
Instead: Stay determined and resilient.
Being an entrepreneur can be tough and very lonely. Challenges arise everyday, often out of the blue, and you can't talk with your team or the ecosystem about many of the issues that you face. (Good advisers and investors can be helpful here.) Resilience is one of the most critical characteristics of successful entrepreneurs.
To quote Jeff Booth, founder and CEO of BuildDirect, who has successfully dealt with his fair share of challenges:
"You are going to get knocked down, and you need to stand back up. You are then going to get knocked down again and again, and you have to keep on standing up. Learn from people who have done it before you. Learn from every experience. The only thing that defines you at the end of the day is whether or not you stand back up."