Over the past five years, I’ve accrued a lot of advice – some of it invaluable and some not so much – as well as lessons learned the hard way. I’ve also collected quite a few notes and reminders along the way. These are not irrefutable truths; they’re simply my observations from my own journey. If nothing else, I hope they’ll help you define your own.
1. If you know it is foolish to learn to drive a car from someone who has never been behind the wheel, use the same yard stick to decide who gives you advice about your startup.
2. There is nothing wrong with learning that you don’t like working for a startup, building a startup, or being an entrepreneur; choosing not to leave a well-paying job to chase a dream is a completely valid decision.
3. Don’t expect anyone else to understand your decision to walk away from security if you choose to launch your own company, but if your spouse doesn’t, think twice about your decision; marriage is tough going no matter what, but it needs both of you pulling in the same direction if you’re going to weather the stress of building a company from nothing.
4. Don’t believe your feelings when you hit the lowest lows or when you arrive at the highest highs; it is the balance of those days that are a better measure of whether you’re coping with the roller coaster ride of entrepreneurship.
5. Don’t confuse someone giving you investment with success; investors tell you if they believe you might have it right, but the customer is the only one who can tell you if you’re actually doing it right.
6. Don’t take investment until you absolutely need it or until not taking it will mean not growing fast to meet market demand; there is nothing wrong with bootstrapping.
7. When taking on family or private investment, founders can still retain control of the growth, pivots or exit of their company, but once institutional capital is invested, a countdown begins and is determined by the investors’ timeline. Be sure your team understands that timeline and the outcomes before accepting venture capital.
8. Some money is far too expensive to accept – whether it is from family, angels or venture capitalists; not all investors bring the same value, and some investments come with so much baggage or future problems that it isn’t worth the runway it buys.
9. If you take on investment that turns out to be more problems than it was worth, don’t expend energy on regret; focus on using the funds wisely to get out to a better position so you don’t ever have to make that kind of deal again.
10. If you find yourself facing a quandary, use your investors as a resource. If you have quality investors, they’ll be invaluable in helping you solve your problem, and if they’re not, better to know that as well.
11. Don’t gossip. Just don’t. You’ll burn bridges with those you throw under the bus and anyone else who decides you are not high enough quality of character to deserve their interest, support or time.
12. Never, ever hire out of gratitude. EVER. Neither of you will end up grateful or even happy if you hire anyone who doesn’t fill a real need in your company.
13. It is not your job to give someone fifty chances to step up and do the right thing, and your investors are trusting that you won’t waste their money on someone who has proven to be a problem.
14. Don’t fire an employee when you’re angry; it could end up being a rash decision that hurts your company’s ability to meet milestones.
15. If you have any inkling that someone is stealing, doing drugs or sharing company secrets, consult a lawyer before a confrontation; you’ll be able to position your company to come out with the least amount of damage.
16. You will never be sorry for telling someone you appreciate their effort or sacrifice, and while praise will not pay their rent, it banks a lot of good will against difficult times in a startup.
17. If you’re generous with telling your team what they did right, they will hear you better when you have to point out what they did wrong.
18. If your startup is a side project to your regular job, don’t lull yourself into complacency by thinking you have all the time in the world to work on it at your own pace. Someone else is out there building something very similar, and they’re going for it with all of their time and money – if you don’t feel the heat, it’s because you’re too far away from the fire.
19. If you are going to be brave and visionary enough to call others on their baloney, be sure beforehand that you’re tough enough to weather the consequences.
20. Don’t be afraid to ask for help from those ahead of you or too selfish to help those following behind.
21. Not everyone who is highly visible lives in a walled garden, and you won’t know if someone is willing to help if you don’t ask.
22. Don’t squander any opportunity someone else makes possible for you; they will definitely remember if you blow it off, and it will be the last time they want to help you.
23. It may seem rude, but it is kindness to not waste even an hour of someone else’s time when you know you have nothing to offer.
24. If you want to connect one of your contacts with someone else you know, ask before you share their information; it could put all of you in an awkward position if that person isn’t willing to help, and it will definitely leave you with less access to that contact than before.
25. Helping others can sometimes be a feel-good distractor that prevents you from working on your own problems and solving your own challenges; be careful about being too generous with your time.
26. The secret to social media isn’t to have the most followers and chasing that goal is probably the most ineffective use of your time with the exception, possibly, of watching cat videos on YouTube.
27. Be authentic, engaging, and interesting if you want to make useful connections on social media.
28. If you can’t figure out how to effectively use social media, emulate Marc Andreessen; he is probably the classiest, savviest user on Twitter today, using his network to challenge the thinking of others as well as his own and engaging with those he knows well or not at all.
29. Using your network well can extend your reach far, far beyond your current circle, but it won’t happen if you’re sending canned messages out into the ether and focusing on your image instead of your interactions.
30. ‘I don’t know’ is a valid response, so don’t pretend to know what you don’t; when your gaps are discovered, you’ll look like a liar and a fraud instead of an insecure entrepreneur feeling inadequately prepared for the question at hand.
31. Build a team that fills in the gaps of each other and of your areas of weakness.
32. If you’re bad at numbers, then make sure someone on your team is good at numbers – and that it is someone you can trust implicitly.
33. If you don’t know how to market, then don’t build an entire team of highly technical individuals who don’t know how to sell; you’ll likely end up with a killer technology and no customers or revenue.
34. No one expects you to be the smartest person in the room, just that you be the one with the clearest vision and ability to lead those around you.
35. Don’t call yourself a successful entrepreneur until you have the numbers or exits to prove it; better to be considered humble than not be taken seriously.
36. Just because it’s written in a blog doesn’t make it so – including this. Think for yourself, question what you read and don’t let someone else’s facts become your own without a lot of due diligence.
It was while interviewing Dale Carnegie for a small newspaper that Napoleon Hill landed a writing gig in 1908 that changed not only his own future but created the concept of the mastermind which became a tool for success for generations to come. The reporter was asked by Carnegie to survey over 500 men – and a few women – many of whom were millionaires and were considered among the most successful individuals in the world. The task took Hill twenty years and culminated in a report that filled several volumes of work and outlined the commonalities of experience and process among those he’d surveyed in hopes of creating a path of success for future entrepreneurs to follow.
While Hill is credited with penning the first published concept of the mastermind, the practice of engaging with a tight circle of trusted advisors dates far before his definition to as early as the legendary Knights of the Round Table who advised King Arthur. And, in fact, many of the innovative ideas put into practice as part of the New Deal which many historians believe were responsible for stopping the downward spiral of the U.S. economy in the 1930’s were the result of the mastermind group which advised then-president Franklin D. Roosevelt.
Over a century has passed since Hill described the role and value of the mastermind, and still today it is a very powerful tool for entrepreneurs. As part of our goal to empower women entrepreneurs and inspire them to think bigger, bolder and better, my cofounder of Hautepreneurs, Jessica Eaves Mathews and I established a mastermind for our group. We meet with a small number of fellow women entrepreneurs once a month, and I have learned first-hand the value of accessing trusted collective knowledge, experience and creative thinking.
Here is why every entrepreneur needs to be a part of a mastermind:
No Complacency Allowed
As the founder of a company, every day is filled with demands and needs coming fast and furious from a multitude of directions, including customers, employees, vendors, investors and beyond. It is easy to allow your time to be consumed with addressing issues as they arise and to not to push ourselves into new areas of growth – the very thing that must happen if we are to stay relevant and capture more of the market. Meeting with a group of peers who all live with the same level of demands means that you will likely get very little pity or license to go easy on yourself. Whether you are afraid to embrace the risk of growth, face the upheaval of firing an entrenched problem employee, or of forcing yourself to slow down to gain proper perspective, a mastermind group will push you beyond complacency and auto-pilot, challenging you to address problems, step up your game and lead with more authority and courage.
Safe to be Vulnerable
There is this scene in the movie You’ve Got Mail where a famous author comes rushing into the book store worried about the possible loss in business due to a new big-box book seller opening nearby that could mean the little store might be closed before her upcoming book signing. The accountant puts on a brave face and declares, “No difference!” despite it being patently untrue. As an entrepreneur, we quickly learn that it is imperative to put on a brave face, wear our courage with a smile, and push forward into the future with all confidence despite living dangerously close to the edge of failure. We often feel isolated and alone, because we can’t let our guard down and talk about the moments when we are terrified that perhaps all we’ve done is build an intricate house of cards that will come tumbling down at any moment. These are the moments of fear and self-doubt that only another entrepreneur can understand. When members of a mastermind are bound by a legal NDA (non-disclosure agreement), there is an incredible freedom that comes with that level of trust. We can talk about the fear, about how close we’re pushing to the edge, about the level of risk we’re living with. And what we discover is that we are far from alone – that every entrepreneur out there is living with more risk, more fear, more worry and less runway than anyone else might be willing for. And sometimes, in the shared experience of learning we are not alone in our fears or in our willingness to take calculated risks, we can begin to accept that our reality and our choices are not so crazy or stupid as they sometimes seem at three in the morning when we haven’t yet figured out how we’re going to meet the lofty goals we’ve set for ourselves and our company.
Access to Variety of Expertise
The best masterminds are organized with a similar level of success and drive but from varied backgrounds and industries. When you seek the advice of others within your industry, you can begin with a higher level shared knowledge that makes it easier for your peers to understand the nuances of your current challenge, but what it won’t get you is the fresh perspective that comes with entrepreneurs who work within a very different industry and approach your challenge from a unique history and experience. When you can tap into the varied experiences, expertise and talents of successful entrepreneurs in different industries, you’d be surprised at the creative approaches that are suggested that often solve your problem in a way you would have never thought of on your own.
Steel Sharpens Steel
For a mastermind group to deliver the most value for all of the members, it is vital that the group be of similar levels of success with similar goals for growth. If the group includes a mix of powerhouse, highly driven leaders and more casual business owners, the friction of values will eventually lead to all of the members feeling that the group is not delivering enough value for the time expended. The leaders will feel frustrated and those who are happy with less pressure will feel disrespected. When the group is created with careful consideration of pairing the level of goals and intensity of drive among the individuals within the group, and when it is kept small enough for each in attendance to have enough time to feel heard and supported, the members will leave with a clarity of focus that only comes from steel sharpening steel.
Being a part of a mastermind where I can bring the unique challenges I have encountered as our team grows APPCityLife into a global platform – and where I can draw from my own experience to shed new light on the challenges of my fellow members are facing – it has helped me understand the real value of making ourselves accountable, vulnerable and available to our peers. With the right kind of mastermind, entrepreneurs gain a level of support and safety that is rare within the startup world.
A lot of times when we launch a startup, we’re like a duck out of water. We have no clue what steps to take to launch a business. We ask help from others who are more experienced, and we depend on their guidance to help us meander through the challenges of getting a business off the ground.
But at some point, a founder has to stand up and decide that it is time to be in charge.
When I was selected to pitch in front of investors from across the United States during an investor’s summit, I was still figuring out how to be a leader. I had a lot of confidence and believed passionately in what we were doing, but I’d also just brought on a team of developers and co-founders who were far more experienced than me. I was feeling a bit uneasy about how to lead us forward.
For several weeks, I met with a team of mentors from varying areas of expertise who were all tasked with helping me prepare for my presentation during the summit. Week after week, I received divergent advice, sometimes even completely opposing instructions from my team of mentors:
Less words and more photos on the pitch deck.
More words and less photos on the pitch deck.
Scrap the images; don’t scratch them.
Ask for more money. Ask for less.
During the early mentor meetings, I would try to please whatever looked to be the consensus of the group and would shift directions, change my pitch deck, change my talk … all in an effort to get the approval of this team of experts who I saw as more knowledgeable and experienced than me.
And then one day, in frustration, I pushed back and started telling them what my vision was, what I knew I needed to say, what I wanted my pitch deck to look like. The results were remarkable.
Once I truly embraced being in charge, it made all the difference. I realized that each of the mentors did exactly what they were supposed to do – give me their advice and feedback based on their own experience and knowledge. It wasn’t their job to give me consistent feedback. It was my job to take all of that feedback and use it to clarify my own position.
Once I owned my own vision and message, this group of mentors with very different opinions all came together behind me and expressed approval for the way the presentation was shaping up.
No one wants to follow someone who doesn’t know how to lead. If you are a founder, learn to lead. Learn to own your vision and have conviction. Stick a stake in the ground and declare what it is you’re doing. What problem are you solving, and why is your solution so important? Understand that and let it drive everything you do. You’re the boss, so when you need to, push back and draw a line about who and what you are as a leader. It won’t guarantee success, but not knowing how to lead will guarantee.