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Owning Your Shortcomings: A Superpower

Today I had independent conversations with two entrepreneurs at different stages of their journeys. One just exited his second company and is beginning to think about what problem he wants to solve next. The other is still building his first company. Both of them mentioned that they’d spent considerable time identifying what they need in an early core team and recruiting people who fit those criteria.

I went a bit deeper, and both revealed gaps in their abilities or experiences that could prevent them from being successful. They’re both smart, super talented, and successful—and very self-aware and upfront about their limitations.

No one is good at everything. We all have shortcomings. But not everyone will admit to them. That’s too bad because being transparent about shortcomings can actually help founders. Sounds counterintuitive, I know. Many founders think they have to be great at everything—superhuman, practically—but that’s not realistic or sustainable. Acknowledging their shortcomings can help them understand what gaps they need to fill to round out their team. Recruiting efforts can be more focused and attract candidates who know what they’re good at. And it supports a culture of teamwork—people pay attention to what the leader does and follow suit.

Founders who want to build great businesses should consider being transparent about their shortcomings. It’s a great way to turn something that could be perceived as a negative into a superpower that can propel you to new heights.

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Office Politics Will Undermine Company Culture

I listened to a founder discuss the dynamics of his company recently. He raised capital and the business is growing aggressively. He’s adding to the team and giving more responsibility to legacy team members. There’s more hierarchy (a good thing) but also more politics, which the founder hates. Decision-making has slowed, and receiving individual credit is prioritized over teamwork. They’re playing the Game of Thrones.

I haven’t worked in a large organization in many years, but I remember that when I did, the politics were apparent. I didn’t like navigating that environment. It felt like a popularity contest. I ended up leaving for a variety of reasons (not just that), but the experience stuck with me. When I started my company, I wanted to avoid politics. I think we accomplished that.

Culture is a key ingredient in success. I think this founder is right to be concerned about office politics eroding the culture of his company. I hope he can get his team thinking with a “we” mindset again.

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Build a Company, Not Just a Product

I recently spoke with a founder who’s had some turnover on his team. He’s an early founder and doesn’t have a working MVP yet. He said that his highest priority is finishing the MVP, which he’s considering doing himself. He isn’t worried about trying to replace his team.

This founder has hit a rough patch on the people side of the business, and he’s understandably frustrated. I’ve been there as a founder, so I get it. But it’s part of the journey —most founders experience it at some point.

This founder wants to forgo replenishing his team and focus intently on building a great product by himself. He’s very smart and will likely build something impressive. The problem is that building a product isn’t the goal. The goal is to solve a problem extremely well and get customers to pay for the solution. To achieve it, product development isn’t enough—you also need to develop other functions, including marketing and sales. To put it another way, you need to build a company.

Early-stage founders should keep in mind that their goal is to build a company. And that requires a team.

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Never Be Above Getting into the Weeds

Founders usually start off doing everything. They’re the glue that holds the company together in the beginning. They’re in the weeds executing to move the company forward. As the company grows, that’s not scalable, and founders begin delegating (or they should). This usually means they’re managing the executors or managing the managers. If done correctly, this allows founders to look at things from 50,000 feet, metaphorically speaking, and think more strategically about the business.

Having to think only high-level about the business is a great thing. I remember when I was able to do this. It felt like I was lifting my head above the clouds and seeing the horizon clearly. Once you’re above the clouds, it can be hard to go back.

Today I spoke with a founder who has removed himself from the weeds of his business, but it isn’t going well. The business isn’t performing as it should, and he knows he needs to replace the people who are executing (or failing to execute). The problem is that he doesn’t want to go back to executing. He can’t wrap his mind around doing that type of work again.

I lived this situation myself in the early days of CCAW, so I can relate. I delayed making changes because I didn’t want to get back in the weeds of a specific area of the company. That delay proved costly and the business suffered. The business lost so much traction that I was ultimately forced to go deep into the weeds to identify the issue and reverse the damage. I had waited so long that we had a razor-thin margin of error. With the support of others team members, I dug in and figured things out. We reversed the trajectory, and I was ultimately able to get back out of the weeds. With the problem solved, the team thanked me for jumping in alongside them. They hadn’t expected it (neither had I!), and they appreciated it.

My lesson from this was that I should’ve always been ready to jump in and do what was needed. I was the founder and it was my company, but I wasn’t above getting into the weeds. Founders do what needs to be done, even when they don’t want to.

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Commit to Your Solution, Not Just the Startup Life

I was chatting with a founder friend about early-stage entrepreneurs. This person was a founder for over a decade and then sold his company. He’s lived it and achieved what many founders aspire to, a liquidity event. During our chat, he mentioned that early founders need to be committed to the problem they’re solving, not just fixated on being a founder or being part of a startup.

He’s right. He and I both spent over a decade building our respective companies. There were many tough periods and trying moments. Those are the times that test founders, and their commitment to the problem determines whether they pass the test. If a founder cares mostly about the title or the “glamour” of startup life, they probably won’t be motivated to stick it out during tough times.

Starting a company is hard, and building it is often a journey of a decade or more. If you’re considering being a founder, make sure that what you’re working on excites you enough to make you want to push through thick and thin.

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More Early Founders Have Coaches

Over the past few months, I’ve been hearing more early-stage founders say they have coaches. Some sought coaching on their own. Others did so because it was suggested.

I’m a fan of coaching and have experience with it myself. Quite a few of my founder friends have also been coached. It’s a great way to foster self-awareness and work toward becoming the kind of founder you aspire to be. It’s not always fun or easy. A good coach will tell you things you don’t want to hear and have you do exercises you’d rather not do. But the effort is usually worth it in the end.

It’s great to hear more early founders openly discussing coaching. I think this a big plus for them, and I hope the trend continues!

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Meaning Is Beginning to Matter

A friend and successful entrepreneur who recently sold his company shared an interesting prediction with me. Purpose is what motivates most people. The events of 2020 helped many people crystallize what matters most and what motivates them. My friend thinks that companies whose only purpose is profit showed their true colors during 2020, and their employees took note. He predicts an exodus of employees from these companies over the next year or so. Companies that have a clear purpose above profits have built significant trust with their employees and communities with their actions. They are likely to see an influx of people wanting to join them.

On various fronts, 2020 was extreme. I’d imagine almost every company was affected to a lesser or greater degree.

I agree with my friend’s observation. More people are professionally motivated by purpose rather than money. I think this was happening before 2020 but that last year accelerated the trend. I’m not sure if this will cause people to leave their jobs in the short term, but I believe it will be a bigger factor in recruiting going forward. More candidates will judge companies by their purpose.

So, what does this mean for early-stage founders? You can’t build a great company by yourself. You need great people to help you get there. If this trend continues, it could be a boost for companies led by missionary founders. Founders driven by success or financial gain may find themselves at a recruiting disadvantage.


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To Be a Great Leader, You Need a High EQ

One of the toughest situations I had to navigate as a founder was a key team member threatening to leave my team. During a strategy session about an important topic, Bob and I saw things differently. Neither of us backed away from our position, and it turned into a heated debate. We were respectful of each other, but later that day I received an email from Bob saying he would like to leave the team because we didn’t see eye to eye. Bob was extremely smart and talented. He owned all the details of a critical part of the business. Translation: it would be hard to replace Bob, and a critical part of the business would come to a standstill if he left.

I didn’t realize the seriousness of the situation until I read Bob’s email. I immediately realized that it could spiral out of control unless I handled it correctly. I got Bob on the phone, and we listened to each other’s viewpoints (instead of pushing our own). I told him I valued him as a team member, and we agreed to sleep on things.

I felt there was more there, so over the next few days we talked it over and got to the root of his frustrations. I learned that it had nothing to do with what we were originally debating. The company was growing, and Bob’s role was becoming more demanding. He didn’t understand why he was being asked to take on many new responsibilities. This was news to me, but once I understood the problem I came up with a solution.

I realized I hadn’t articulated my vision for where the company was going, so the extra work didn’t make sense to Bob. He didn’t understand how he fit in. He just felt overworked. I started communicating my high-level vision more clearly and frequently to the entire team so that everyone would understand their importance to making the vision reality. I transitioned certain responsibilities away from Bob and hired someone to work closely with Bob and take them on. We put the plan in writing and agreed to it. Everything was back on track. Bob and the rest of the team understood the vision and were satisfied.

That situation was a great lesson. I learned that being a leader is not just about being hard-charging and executing. It’s about people, too (other people—not just you). Leaders need to have emotional intelligence and awareness to understand what your team needs (even if they can’t—or don’t—articulate it) and provide it.

Cultivate this ability in yourself. Your team will run through walls for you.

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You Don’t Have Unlimited Runway

Speed matters to a start-up’s chances of success. Let me explain. Most founders have a defined runway, even if they don’t realize it. They have a certain number of months or years to achieve a certain amount of traction (e.g. get 20 customers). If they don’t do it, it’s game over. Think of a plane during takeoff. If it doesn’t reach a certain speed and elevation before the runway ends, it’s in serious trouble. Game over for a founder can mean running out of cash, other resources, or family support.

Getting traction requires work. Founders have to execute. Doing nothing will lead to failure. Founders understand all of this. But what some don’t realize is that speed of execution is equally if not more important. They can take the right actions, but if they’re too slow about it the outcome won’t be what they’re aiming for. Founders have to be aware of time and make sure they’re executing and making progress toward their goals quickly. Otherwise they’ll find themselves staring at the end of their runway.

If you’re a founder, be mindful of how quickly you execute. If you’re not moving along at a good clip, consider tracking it and discussing it among your team.

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Jeff Bezos in Transition

Today Jeff Bezos announced that he will step down as CEO of Amazon later this year. Last week, I wrote about journeys cycling around. I couldn’t help but think about that post when I read the announcement. Jeff will still be involved with Amazon. He’ll be chairman of the board (to which the CEO reports).

Jeff pointed out that this transition will give him time and energy for other initiatives outside of Amazon, including the Washington Post, Blue Origin, and Bezos Day One Fund. It sounds like Jeff is working toward the “rebirth” I discussed in last week’s post.

Amazon is an amazing entrepreneurial story. The fact that Jeff led this company from the idea stage to over 1.3 million employees and a $1.7 trillion market capitalization (i.e. valuation) says a lot about him. He’s a legendary founder who I suspect will go on to do even more amazing things after Amazon.

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