Founding teams have been on my mind lately. I’m curious about what traits increase their chances of success. I’ve heard many opinions on this, but the Hipster–Hacker–Hustler concept kept coming up. I decided to look into it further. Here’s what I found:

• Hipster – The Hipster focuses on the product being desirable to customers. They think about things like user experience and product design. They tend to be in tune with what’s trendy and cool. They have a unique customer-driven perspective.
• Hacker – The Hacker is the builder. Building new stuff excites them and they can focus intensely on it. They are driven by data and logic. They see the world as black and white and may not have as much charisma.
• Hustler – The Hustler makes sure that things get done. They relate well with people and are persuasive. They can hold people accountable to results, sell to customers, and rally people behind their vision.

I think this is a great template for a founding team. It probably won’t work in all instances, but it’s a good framework to consider.

I’m a Hustler for sure. I’m laser focused on achieving the desired result, enjoy talking with people, and take psychological ownership of what I say I’ll do. As I kid, I convinced neighbors and classmates to become customers. I bootstrapped CCAW from nothing to eight-figure revenue. All by being a Hustler. At times it was painful, but I learned a lot about others and myself. I can see now how a Hipster and Hacker could have added a lot of value and accelerated CCAW’s success.

I encourage rising entrepreneurs to consider the makeup of their founding team. Being a solo founder can work against you. So can having a team of founders with similar expertise and perspectives. Diversity is important and can lead to amazing things!

Today, Memorial Day, I'd like honor the fallen soldiers . Their ultimate sacrifice is for our country is worthy of this day and I'd like to say thank you!

I hope everyone had a safe and healthy memorial day with loved ones!

A new entrepreneur asked where ideas about critical features of CCAW’s system came from. These features allowed us to streamline our management of large amounts of data and set ourselves apart from competitors. They ultimately became the foundation for growing rapidly while keeping to the quality standards we were known for. My response? Conflict. The entrepreneur was surprised.

When a challenging problem needed to be solved, I’d have a whiteboard session with company leaders. We’d agree on what the problem was and then begin debating how to solve it. We often were of different minds. Sometimes our disagreements were intense and tempers would flair. Usually, everything worked out—we would come up with an amazing solution that borrowed from everyone’s perspective.

To make sure our conflict stayed healthy, we had to establish ground rules. Basically, we adhered to the golden rule: we had to treat each other as we wanted to be treated. When things got heated and we were about to break that rule, we suspended the meeting until everyone was calm. We reminded each other that everyone is entitled to their opinion and it’s OK to agree to disagree.

My big takeaway from those sessions was that healthy conflict can bring good outcomes. We didn’t see eye to eye, and we each thought we were right, but we respected each other. Genuinely listening with the intention of understanding allowed us to view the problem through a different lens. After hearing everyone out, we saw the problem completely differently. That helped us see a different path to a solution. I often noticed that when they understood a team member’s perspective, people would have a burst of ideas. We fed off each other’s ideas until we reached a solution that we all thought was ideal.

I don’t like to argue, but I have an appreciation for the value of someone else’s perspective. I may not agree with it, but I enjoy the process of trying to understand it. When you’re building a company, you’re often trying to solve problems that others can’t solve. Constructive conflict is a powerful tool that mature teams can use to solve problems in unique ways.

How has constructive conflict helped you solve a problem?

One of the most consequential decisions I made as an entrepreneur was to seek out mentors. Over time I had a few as CCAW transitioned. It took me several years to find my first really good mentor, but when I did it made a world of difference. At the time, CCAW was doing around $500,000 in annual revenue. The company was just me and one team member. My mentor was in a different industry, was doing around $60 million in annual revenue, and had more than a hundred employees.

I recently reflected on what made the relationship so impactful. There are lots of things, but one especially stands out: credibility.

When I described a challenge, my mentor could relate to it because years earlier his company had been at the stage where CCAW was. He drew on the specific experiences that helped him resolve the same challenge or one that was similar. His credibility came from having already achieved what I was trying to achieve. He shared his blueprint for success, which comprised knowledge amassed over many years. He essentially laid the path to success at my feet. I still had to walk the path, but I didn’t have to figure out where it was or what it looked like.

I believe that everyone could benefit from this type of wisdom and should consider establishing a relationship with a credible mentor. To increase the likelihood of a fruitful mentorship, I encourage people to first decide on the answers to two simple but powerful questions: What am I trying to accomplish? Has my prospective mentor successfully done the same sort of thing? If you can’t answer the first, you’re not ready to be mentored. If you can’t say “yes” to the second, you haven’t found the right mentor.

When seeking knowledge from another person, always consider whether he or she is credible. On my business journey, the wisdom of credible people has been a game changer many times.

For years, I’ve struggled with managing certain relationships. I do fine with family and close friends—I’m in touch with them regularly. (Mom may beg to differ sometimes.) It’s people outside this inner circle that I have trouble keeping up with. They get my attention at random times. Someone will pop into my mind and I’ll reach out to them when I get home (if I don’t forget).

After acknowledging my weakness, I decided to do something about it. I did some research and spoke with people about what I was trying to do. A close friend recommended the Fabriq app. It’s new and still evolving, but I decided to give it a try. I’m using it for my personal contacts. (I take a different approach to nurturing professional relationships.)

Here are some of my takeaways:

• Circles – The app triggered me to think about the type of relationship I have with each person and what circle they’re in (inner, middle, outer, etc.). This exercise took a bit of time, but it was very helpful.
• Schedule – You set the touch point frequency for each contact, and the app nudges you when it’s time to reach out. This has been useful—it’s helping me work toward establishing a habit.
• Reminders – Custom reminders can be set for important dates, follow-up activities, and anything else you like.  
• Notes – Information can be added for each contact. After a call I sometimes create a note about something important that I just heard but that I’m not likely to remember. I look over my notes about a person before calling them next time.
• Initiate contact – Texts and calls can be initiated from within the app. There are templates for conversation starters too.

Overall I’m pleased with the app. It’s not perfect, but it has improved how I manage relationships. I like how proactive Fabriq’s team is. They’re constantly improving the app, so I predict that it will get better over time. That said, it’s not a silver bullet. I still have to make the effort to use the app consistently.

What’s your strategy for managing personal relationships?

Yesterday I got an unexpected call. It was a group FaceTime from a few old friends. They were celebrating Cinco de Mayo, quarantine-style of course, and wanted me to join them. There were five of us. We live in four different states in three different time zones. We seldom see each other face to face: we’re all in the same place once every couple of years, if we’re lucky, because of the planning and travel required.

Today I reflected on the call. We have a regular group text, so we’re connected. We call each other for one-to-one conversations too. Even with all this, FaceTime enhanced our communication. Why?

Here’s my theory. Throughout history, most of us have communicated using our

• voice,
• hearing, and
• eyesight.

Text messages engage only our eyesight, and only in a limited way—we can look only at words, not faces. Tone, humor, and other subtleties are difficult to convey, though emoji help.

Phone calls let us use our hearing and voice. Humor, tone, and mood are more easily understood. But calls don’t require sight and, like texts, don’t allow us to communicate through body language (for example, facial expressions).

FaceTime and other video platforms allow us to communicate verbally and nonverbally. Tone, humor, mood, and body language all have a good chance of being understood.

I think video is powerful because it engages our voice, hearing, and eyesight. It’s the next best thing to communicating in person. Using all three just feels more natural.

Video isn’t new. FaceTime, Zoom, WebEx, Houseparty, and others have been around for years. But use of these tools is now soaring. People of all ages who once relied on traditional phone calls and in-person communication are now embracing video.

We’ve seen rapid-fire mass adoption because the pandemic is keeping people apart. Restrictions on in-person communication have created a void, and video-based tools are filling it. They allow us to communicate in the way that feels most natural—using our voice, hearing, and eyesight.

Face-to-face communication is irreplaceable, but video will play a much larger role in people’s lives from now on because we’ve been compelled to get used to it. I predict that entrepreneurs with experience in video or ideas about how to enhance video communication will be highly sought-after by investors and venture capitalists.

How do you see communication evolving?

I recently spoke with an entrepreneur whose business is falling off due to the pandemic. He’s starting to see about a 25% drop in customers and revenue. We talked about rightsizing to avoid unprofitability.

We categorized each of his expenses as fixed or variable. Most of the latter should decrease effortlessly because he’ll be using products and services less. I encouraged him to try to reduce fixed expenses by proactively contacting the people he’s paying and letting them know his situation. He told me he’s begun doing this and has been able to negotiate some savings—most notably, a 40% reduction in rent for the next few months. It turned out that his landlord appreciated the proactive communication and wants to keep him as a tenant. No doubt it helped that the entrepreneur has paid on time for five years and rent payments aren’t the landlord’s primary income.

My big takeaway from this conversation is that proactive communication is powerful. He didn’t procrastinate until things became dire. He acknowledged what’s happening, came up with helpful ideas, and openly discussed the problem with other people it affects. The upshot was an amicable win–win resolution that will help his business survive the downturn and avoid disasters like bankruptcy and lawsuits.

I encourage anyone navigating rough waters to look reality in the face and communicate honestly with other stakeholders sooner rather than later. What you don’t ask for, you won’t get.

How has proactive communication kept you from running aground?

I’ve shared my views on the importance of bidirectional relationships and treating investor relationships as partnerships. Today, I write about another relationship truth. For most entrepreneurs—and everyone else, for that matter—there will come a time when a relationship is no longer a good fit. This has happened to me when values—mine and the other person’s—don’t align.

At CCAW, we had done business with a certain vendor since our earliest days. Eventually, we bought more from this vendor than from any other, and we’d become one of their biggest customers (for the products we purchased). As with any relationship, there were ups and downs. I was tech focused and pushed them to upgrade their technology so we could integrate our systems and grow the relationship faster. They thought the old manual way worked just fine. Despite this, we continued working with them. It got to the point that CCAW spent about $1 million with them every year.  

It all seemed to work, until it didn’t. They began to gripe about their other customers to me and show attitude to our service team members. For years, I’d met annually with their executive leadership. After noticing these changes, I began inquiring about their company vision and values. Maximizing revenue and profit was their vision, and they had no clear values. It all started to make sense. As they grew, the lack of a clear vision and values caused them to stray from what made them successful.

Our internal data showed that sales of their products accounted for half our annual gross profit. I’d have to figure out how to replace it before I even thought about switching vendors. I was basically married to them. I decided to unwind and replace the relationship slowly over two or three years.

Within a few months, the working relationship between our service team and their sales team tanked, to the point that a blowup reached my desk one day. I reviewed the situation and knew I had to do something. The vendor was eroding our service team’s morale and taking up too much of our operations leader’s and my time. I decided to pull the plug on the relationship effectively immediately. Remember: half our gross profit! I was making CCAW instantly unprofitable. Needless to say, I was pretty nervous. I was under the gun. It was either replace that lost profit or go out of business.

Then a funny thing happened. Because our team didn’t have to deal with this vendor, it had so much bandwidth and time that we were able to invest in both new and existing vendor relationships. In a month or two, we had regained all the lost profit and then some. My service team was happier, our leaders’ time wasn’t being wasted, and the company was back to growing in a healthy and profitable manner.

Upon reflection, I now realize that I made rookie mistakes:

• Hire slow – I focused on growing the relationship with the vendor as quickly as possible. What I should have done is evaluate them more thoroughly before doing business with them or get to know them better before allowing the relationship to reach material scale. I should have found out what they stood for, and why.
• Fire fast – When you make a hiring mistake, it’s best to correct it quickly. Fire them right away. The longer they’re around, the more serious the damage becomes. I tried to ease the vendor out over time. Instead, I should have ripped the Band-Aid off and endured the short-term pain. I could have saved my team a lot of time, energy, and frustration.

We were lucky that things worked out well. Lesson learned: pay much closer attention to the values of people and organizations I associate with. If the values revealed by their actions don’t align with mine, I politely pass. It’s easier to avoid them than to rip and replace.

How has alignment of values affected you?

I’ve shared my views on the importance of bidirectional relationships, which I believe is one of those good-life principles. But for entrepreneurs, understanding how to approach relationships with investors is imperative.

Don’t view a good investor as a cash machine, but rather as a partner in building your business. Yes, they provide capital and seek a return on it, but they can also add value in a variety of other ways. They can make warm introductions to potential customers or vendors. They can tap their networks to help recruit for key positions. They can help you navigate turbulent times by sharing their experiences and strategizing with your team. A good investor may invest a lot of time as well as money. They aren’t just making an investment in your company—they’re investing in the founder—you—too. Quite reasonably, they are likely to want to get to know you before making an investment. In fact, they like to establish the relationship long before they commit funds.

These ideas may help entrepreneurs approach investor relationships correctly:

• Pitching – Don’t expect to walk away with a check. Their feedback can be many times more valuable, especially if you’re early stage. Pay close attention to it. And ask questions. Two good ones: “Is there anyone you think I should know?” “Can I help you in any way?”
• Updates – Send them a clean, succinct monthly update. This will help keep you top of mind. Have a clear ask.
• Touch base – Periodically reach out to ask them what they’re up to and how they view certain markets. Share some of the things you’re doing that may not make the update. Ask if you can connect them with anyone or help them in any other way.
• Make connections – If you know someone who could benefit from knowing the investor, or vice versa, make the intro. Both will appreciate it.
• Share knowledge – If you learn something that you think an investor could benefit from knowing, pass it on.

Approaching relationships with investors correctly can be a game changer. Start developing them early.

Sheltering in place for over a month has been . . . weird, let’s say. A lot of people are now working exclusively from home. Travel is limited. Routine activities like grocery runs are potentially hazardous to health. COVID-19 stats in the news are frightening. After reflecting on all of this today, I realized that one thing is helping me cope: bidirectional relationships.

I’m reaching out to more people. Others are reaching out to me. Each of us listens to what the other has to say about our experiences navigating the pandemic. What lessons have we learned—good and bad? What information do I have that they may find helpful? And vice versa? What do we think about the state of the world—and what do we believe about the future? To be supportive and convey that I care about what they’re going through, I always end by asking if there’s anything I can do to help them.

These conversations usually energize me. This is partly because of the social interaction, but beyond that I also enjoy feeling that I helped someone and at the same time invested in the relationship.

A good friend recently shared this analogy: “Relationships are like bank accounts. If you make withdrawals but never make deposits, your account will become overdrawn, and eventually it will be closed.”  

Are you investing in your relationships—or draining them dry?