This week, I’ve listened to two founders who are targeting enterprise companies as customers. One, “Alan,” landed a major one with no product and a pitch deck. The other, “ Bob,” has a working product but hasn’t yet been able to persuade anyone to use his platform (which is great, by the way). The big difference? Relationships.

Alan has years of experience and relationships with people who trust him. He leveraged them to land his first customer. Bob is solving a problem in a space where he doesn’t have relationships or experience. He has to earn the trust of potential customers, and that takes time. Alan has founder–market fit; Bob doesn’t. This doesn’t mean Bob won’t be successful; it just means he may have a tougher journey. I learned this lesson the hard way when I was a founder.

Many factors increase or decrease the chance of success. Founder–market fit is one of them. If you’re an aspiring founder with an idea but no founder–market fit, ask yourself if you’re the right person to solve the problem. If you believe you are, forge ahead!

Today I attended Outlander Labs’ Speaker Series. This month’s speaker was Hamet Watt. He has a diverse background that includes being a venture capitalist and entrepreneur. He’s currently CEO of Share Ventures, a venture studio, and used to be co-founder and chair of MoviePass. Here are a few takeaways from today’s conversation:

• Harmony vs. consensus – Harmony on a team is good. It means people respect each other’s opinions. Consensus in decision-making ends in watered-down decisions. The drive to consensus smooths the sharp edge that’s needed for a good idea or decision to get traction.
• Instincts vs. conviction – Founders need great instincts more than they need conviction. If they don’t have good instincts, they’ll be convinced of the wrong things.
• Energy – It’s important for founders to manage their energy. Sometimes you have to sprint . . . but to finish the race, you must pace yourself. You need to be able to continue running even after hearing “no” over and over again. Hamet views this as a mostly mental trait.
• Prioritization – People who ruthlessly prioritize to get things done make good founders. They understand everything won’t get done, but they’re sure to complete mission-critical tasks.
• Conversations – Investors want to have conversations; they don’t want to be pitched. Investors are human beings who want to partner with people. Hard to do that if communication isn’t bidirectional.
• Ideal investor – Founders should look for investors who allow them to be themselves. It’s easier over the long haul to work with someone who accepts you and sees your personality as a strength.

Hamet has a unique perspective on things and it was interesting to hear him explain it. He also shared an interesting story from his MoviePass days.

I’m excited for Hamet and Share Ventures and can’t wait to see the businesses he helps start!

This past weekend, I had an issue with an expensive product I purchased a year ago. I was frustrated that it was defective and worried it might be out of warranty. I called their customer service number on Saturday morning and had a pretty good experience. I sent a few pictures while I was on the call. The rep offered to send me a replacement free of charge and alternatively gave me the option to upgrade to the latest product for a small upcharge. In the end, happy they stood by their product, I decided to upgrade.

A lot of companies focus on getting the customer and closing the deal. I’m of the opinion that how you treat the customer post-transaction is equally as important. Giving your customers a satisfying experience after the deal is how you establish loyalty and turn them into evangelists. In my situation, this company has probably gained a customer for life because of the way they resolved my problem. That’s what I’ll remember, not the problem.

Regardless of the stage of your company, remember to treat your customers well after the sale. Doing so will help you build a base of loyal repeat customers you can count on!

A founder once asked me a question that caught me off guard: “Did you have trouble sleeping when you were building your company?” As soon as he finished asking the question, I knew exactly where the conversation was headed. “Yes,” I said. He told me he’d started waking up in the middle of the night thinking about his company and had a hard time going back to sleep.

He’s not the only one. When my company began to grow rapidly, I started waking up in the middle of the night. At first I didn’t pay much attention to it, but eventually I noticed a pattern. I’d be exhausted from a long day and go to bed at a normal time. I’d sleep hard and then wake up around 3 or 4 with my mind racing. My thoughts usually revolved around two things. One was whatever I was most worried about . . . the thing that might sink my company. The other was ideas. It was weird, but I’d have a burst of ideas when I’d awaken in the middle of the night.

Sometimes I was able to go back to sleep and sometimes I wasn’t. Eventually, I realized that not getting enough sleep wasn’t good for me and was affecting my productivity during the day. I decided to do something about it. I researched sleep (including mattresses) and began working out again. I created the ideal sleep setup (or so I thought), and I had an outlet for stress and a regularly scheduled time when I couldn’t think about work (or I’d drop a weight on my foot). I eventually began sleeping through the night again. My energy level and productivity increased.

During that period, I asked a few founder friends if they ever woke up in the middle of the night. I was surprised to learn that a lot of them did. How they dealt with it varied, but the theme was consistent: they’d be thinking about their company as they lay awake in bed.

I’m not a sleep expert, so I can’t give advice about sleep to founders. I will say that I slept better and was a more productive founder when my routine included two things: scheduled time to release stress and intense focus on something besides my company. The latter is harder to achieve. Luckily, working out checked both boxes for me.

Many years ago, I was explaining what my company did to a good friend. All she knew was that I was an entrepreneur building a business. My explanation included details about the industry and lots of industry jargon. At the end of it, she said, “I don’t really understand what all that means or what you do, but it sounds cool. I hope it turns out well for you.”

This week I spoke with a founder who made the same mistake. After listening to him pitch his company, I still wasn’t exactly sure what it did. Conveying what you do in simple terms is important, and it’s usually a sign of a strong founder. Making it easy to understand what your company does and how it creates value for customers is the first step in getting people to support it.

All those years ago, when I heard my friend’s feedback, I backed up and rephrased. “We help connect consumers to hard-to-find auto parts using technology.” That time, she got it! And she gave me the names of a few people she thought I should connect with who could help my business.

If you’re a founder or considering entrepreneurship, make sure others can understand what you do. If they don’t, simplify it.

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A few months ago, I met with a founder who asked my opinion on the current state of his company. I said the salaries he was offering were large for an early-stage startup. The people earning them were qualified and deserving, but the company couldn’t afford-big corporation salaries. It was burning too much money every month and needed to double or triple for that level of payroll to make sense. I told him that I projected he would need to either reduce salaries or raise cash.

I caught up with him this week. He told me that he’d just survived a near-death experience. The company is still growing, but the high payroll caused him to run dangerously low on cash. He reduced his team’s salaries, parted ways with some team members, and raised emergency capital. Doing all of that at once was painful and stressful for him and his investors. It taught him to make a point of having a good sense of the trajectory of his company at all times and to make tough decisions early to avoid getting so close to the abyss.

I never raised outside capital for CCAW, but I did have near-death experiences. I concur with this founder: try not to let this happen. They’re awful. They took a toll on my team and me. Some are unavoidable and you have to do the best you can with the hand you’ve been dealt. (A global pandemic comes to mind.) Others are entirely avoidable.

Founders should always have a finger on the pulse of their company. If this isn’t one of their strengths, they should have at least one person on the team who can fill this gap. It sounds crazy, but so much happens so quickly that it’s not unheard of to wake up and realize you’re almost out of cash. The company’s heart just stops beating, and it may be too late to resuscitate it.

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I was working with a founder on his pitch.  He had a big vision and was passionate, but he needed to fine-tune his delivery. Over the course of our conversations, I realized something. There was a disconnect. How he perceived himself and what others saw was different. He thought his presentation sounded one way, but it actually sounded quite different. Seeing is believing, so I suggested he record his next pitch and send me the recording.

By the next time we spoke, he’d had a realization. He said he’d had no idea how he sounded. With the recording, he could self-critique and correct the part of his delivery he didn’t like.  The recording was the pitch version of looking at himself in the mirror. He saw exactly what everyone else saw.

We decided to take it a step further. Instead of booking time with peers to get their feedback, he sent them links to his recorded pitch. This worked well for a few reasons. First, it forced him to put his best self forward. Who doesn’t watch a video of themselves before sending it to other people? No one. He watched the pitch, redid it, and got it to sound exactly how he wanted before clicking “send.” Second, the recipients could watch it and send their feedback whenever it was convenient for them. And third, he was able to share his pitch with more people and get more feedback than if he’d scheduled one-on-one time with each person.

Recording yourself isn’t novel. It’s a time-tested tool that’s still highly effective. If you want to perfect your pitch, consider tapping “record”!

I recently had an idea I was super excited about. I’ve been considering how to help more entrepreneurs accelerate their success, and I’d only come up with a few ideas that were essentially tweaks of something others have done. When I decided to look at the problem from a different angle, this new idea occurred to me. I was excited about it, but I knew there was a lot I hadn’t thought about. My instinct was to flesh it out more before talking about it. But I soon remembered that I’d taken that approach before, and it was wrong.

I decided to share the idea with a few credible people, and I’m glad I did. These were conceptual conversations, since I hadn’t done a ton of research. Some of the feedback was very positive. Others felt there was value in doing what I was talking about. I already felt good about the idea, and this feedback boosted my confidence. It energized me and made me want to continue to share it. Next, I received feedback from someone intimately knowledgeable about the space. It was more along the lines of “This is an interesting idea. Have you considered X, though?” This person zeroed in on something that might have taken me months to realize and was kind enough to share his wisdom. I appreciate his feedback.

The idea is still just that. An idea. But I’m glad I didn’t hold it close to my chest. These conversations helped me adjust my thinking, made me aware of my blind spots, and boosted my confidence about the idea. I’m not sure where this will end up, but one thing is certain: I’ll continue to share the idea as it evolves.

A few months back, a friend asked me for a favor. It involved doing something with high stakes—something I wasn’t particularly good at and hadn’t done recently. I didn’t think I was qualified. My friend thought otherwise. It was something that I’d always wanted to get better at, so it was an opportunity to gain experience. Still, I was deeply uncomfortable with what was being asked of me.

Over the years, I’ve learned to lean into discomfort when the task will take me in a good direction and aligns with my goals. I’ve usually learned and grown. But I’m not saying it’s always had a happy ending. More than a few of these attempts ended in failure. Regardless of the outcome, though, they ended up being amazing opportunities from which I gained wisdom or experience.

In the end, I said yes to my friend. I took my time to ensure that I did things to the best of my ability, and it was a success. I learned a ton about myself in the process and picked up some skills I’ve used regularly since then.

If you’re offered a chance to do something but it makes you uncomfortable, think twice before turning it down. If it will take you in the right direction or help you achieve a goal, it could be a great growth opportunity

This week I spoke with entrepreneurs working on an interesting product that could help restaurants solve one of their biggest challenges. As we talked, it became apparent that restaurant owners will love the idea. It will make their locations more profitable. But it’s also clear that restaurant employees may be less than thrilled with the product. It dawned on me that this entrepreneur has to convince restaurant owners to pay for the idea and also convince restaurant employees that the product isn’t a threat. If employees don’t buy into the idea, it won’t be used.

Commendably, these entrepreneurs had thought about this. They have a well-crafted message for employees. First, the idea will significantly reduce the time and energy employees spend on a task they hate: from many hours a week to zero. Second, it reduces errors that employees are currently held accountable for. Third, it could give them more discretion in dealing with loyal customers. Finally, it will help with administrative decision-making so what customers want is always available.

These founders have done a great job of understanding who the stakeholders are and what they care about. They have a well-thought-out plan to address concerns. Hopefully this will lead to a smoother sales and implementation process.

It’s important to understand all stakeholders when you’re selling a new product or service, not just the person who will write the check. Getting the product paid for and getting it used can be different. Companies succeed when they’re able to do both. After all . . . is it likely that a product that isn’t used will continue to sell?