Wendell’s Weekly Wins and Whiffs

🏆 Win of the Week: Project Insulnation and Pushing Limits

This past weekend I took time to go hiking in the White Mountains of New Hampshire with a group of type 1 diabetics through Project Insulnation. My friend Chris Roome, who I met through GoBundance, built this thing and it is an incredible mission. The whole point is simple, Type 1 diabetes does not limit you, you can still do anything you want.

We were supposed to do the Pemi Loop but the weather shut that down. Cold, rainy, windy. Out on those ridges it would have been hell and dangerous. So we pivoted. We summited Mount Pierce and Mount Moosilauke on back to back days instead.

What got me was not the peaks, it was the people. Being around other diabetics who are pushing themselves to the limit and refusing to let the disease define them. That is the mindset I live with. That is the mission I support. Type 1 diabetes or not, this is how you approach life.

Here is what I realized this weekend. Most people with type 1 diabetes hear the diagnosis and they listen to the noise around them. They think it is a limitation. They think they cannot do certain things. They think they have to play it safe. And Chris Roome decided to build a community that says the opposite. He is showing people through experience that you can summit mountains, you can push your body, you can dream big, and the disease does not get to be the reason you do not.

That is powerful. That is the kind of mission that actually changes how people see themselves. I spent the weekend with people who are living proof that your circumstances do not define your ceiling. We were cold. We were tired. We were pushing up mountains in brutal conditions. And every single person there was doing it because they refused to accept the story that the world had written for them.

Chris Roome is building something real with Project Insulnation. If you want to check it out go to https://projectinsulnation.com/

The reason this hit me so hard is because this is exactly how I approach everything in my life. Type 1 diabetes or not, your circumstances are not your limitation. Your mindset is your only ceiling. And Chris is creating a community that reinforces that every single day. I am grateful I got to be part of it this weekend.

💨 Whiff of the Week: May Was Amazing. It Was Also Tiring And Stressful.

Real talk. May was completely packed.

Got engaged in the Blue Ridge Mountains. That was incredible. Took a long golf trip with an amazing group of guys. That recharged me. Drove down to Florida to celebrate a friend's wedding. Hiked the White Mountains with the Project Insulnation crew. Then fit in multiple real estate speaking engagements on top of all of it.

Every single weekend I was on the road, the experiences were world class. The memories are going to last forever, but the cumulative weight of that calendar hit different. I am tired. I am stressed about time. I am running on empty by the end of the month even though I was doing things I love.

And here is the real issue. When you are gone every weekend, certain pieces of your business slow down whether you want them to or not. The business does not stop when I am gone, but certain pieces slow down and I am realizing those are pieces I have not delegated or organized correctly yet. It is not a team problem, it is a Wendell problem. I am not setting things up so they run smoothly without me in the room.

Let me be specific about what this looks like. When I am gone, investor conversations slow down. Capital pipeline development slows down. Certain decision making gets queued up waiting for me to get back in the office. My partners are executing their lanes, but there are gaps in organization and clarity around who owns what and when certain things should happen without me having to be the trigger.

Here is what I realized. I have gotten comfortable with the rhythm of running things a certain way. But that rhythm only works because I am in the middle of it. And the moment I step away for a few days, the cracks show up. Not because my team is not capable. They are incredibly capable, but because the systems and the clarity around responsibility are not clear enough to operate at full speed without me there.

This month forced me to see that gap. And that is actually a win in disguise because now I can fix it. I need to sit down with my partners and have real conversations about vision, about goals, about who owns what, and about what needs to happen to keep things moving forward at full velocity even when I am not in the room.

If you are building a business that is dependent on your presence, you have a business that is not a real business yet. It is a job. And I am not interested in running a job. I am interested in building a company. That requires me to get out of the middle and build systems that work with or without me there.

I have made a ton of progress so far, but May showed me that I still have work to do loud and clear.

🎯 Tactical Tip of the Week: Challenge Yourself, Get Away, Then Put In The Work

There is this idea floating around that you have to pick. Grind or live.

That is false. That is lazy thinking.

This weekend was not a win because I took time off. It was a win because I took time off while also pushing my limits. Summiting peaks. Being with people who refuse to let circumstance define their ceiling. That is not rest. That is fuel.

But here is the flip side. Fuel without work is just distraction.

You challenge yourself. You get away. You do things you enjoy that remind you why you are building in the first place. But you also show up Monday morning and do the work. You fix the systems. You have the hard conversations with your partners. You keep building.

The weeks that matter are not the ones where you hide from the grind or hide from life. They are the ones where you do both. Live while you are building. Build while you are living.

That is the balance. That is the level up.

🔦 From the Field: Capital Raising Is a Full Time Job

I have been realizing something over the last few weeks. In a business that needs capital, if you are not actively raising then you are reactively raising.

We are talking with investors. We are starting conversations. But when I cannot dedicate myself more to those conversations we hit timelines where we suddenly need capital and it becomes scramble mode instead of strategy mode.

Here is the truth. Raising capital is a full time job. It is not a side thing you squeeze in. It is not a hustle you add on top of operations. It is the lifeblood of growth and it deserves focus.

One of us needs to spearhead investor relations. And honestly, I think that is going to be me. It is a strength of mine. I actually enjoy it. But here is why it matters. These conversations cannot be superficial, you are dealing with people's money. You are asking them to trust you with years of capital and their financial future.

That means deep dives, transparency and education about the deals. Clear communication about what can go wrong and how you would manage it. Comfort and confidence, not just a pitch and a close.

When each of us narrows our lane, my partners focus more deeply on their operational strengths and I focus on investor relations and strategic capital. That is when we explode in growth. Because right now nobody is fully owning that investor conversation. And in capital dependent businesses that is the bottleneck.

If you are building something that needs capital make sure somebody on your team is making those conversations their primary job. Not a secondary squeeze. Primary.

💰 Passive Investor Opportunities

We are continuing to move deals through the pipeline at Tide and Timber Ventures. If you have been curious about passive investing with our team, reach out. These opportunities fill fast and now is a solid time to have that conversation.

🐝 The Hive CLT Entrepreneurs Network

The Hive community keeps growing. The conversations in that room actually move needles. RSVP for our next event at https://jointhehive.co/

🎤 Final Word

May was overbooked and it showed me where I need to tighten up. But it also delivered wins that reminded me why I am building in the first place. The best weeks do not separate work and life, they blend them. You push limits, you get away, you live and you come back Monday ready to rebuild the systems that let you do it all again.

That is the flywheel. Let's keep it spinning. 💥

Keep growing or die,