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- Wendell’s Weekly Wins and Whiffs
Wendell’s Weekly Wins and Whiffs
👋 Welcome to Wendell’s Weekly Wins & Whiffs — your front-row seat to the entrepreneurial and real estate rollercoaster, complete with high-fives, facepalms, and everything in between. Each week, I’ll peel back the curtain on life as an active investor and business builder: the triumphs that feel like victory laps, the flops that sting like a surprise plumbing leak, and the behind-the-scenes grind of running multiple companies. From flips that soar to admin headaches that test my patience, you’ll get the real, unfiltered scoop on both deals and business operations. Why? Because building wealth isn’t just about properties — it’s about building systems, partnerships, and businesses that can stand the test of time. My goal is to share the wins, the whiffs, and the lessons learned so you can sharpen your own edge in both investing and entrepreneurship.
🏆 This Week’s Win: Building the Team That Will Build the Vision
This week wasn’t defined by deal flow or closings. It was defined by intentional growth. I’ve been putting serious focus into building out the infrastructure behind the scenes, and this week marked a real turning point. Instead of just working in the business, I spent time working on the business, laying the foundation for the team that will carry our momentum into 2026.
I officially hired a social media manager to elevate my personal brand and support the content across all of my businesses. It’s surreal to think that the brand I’ve been building from Hammerhead Capital to Flip Fuel Lending to Tide and Timber Ventures now has someone dedicated to amplifying it. Someone who believes in the mission, sees the vision, and is excited to help tell the story.
On top of that, Tide and Timber Ventures took another major step forward by bringing on a transaction coordinator to tighten our operations and support our growing pipeline. And over at Flip Fuel Lending, I am onboarding a new loan officer to expand our capacity and help us serve more investors heading into the new year. We are still actively looking for additional loan officers as well, since that side of the business is picking up momentum. With these additions, I now have eight employees working across my companies, which is wild to think about. Not long ago, it was just me grinding through every task alone.
And we’re not slowing down. Next week, we begin the search for a deal analyst to join the Tide and Timber Ventures team. Adding this role will help us evaluate more opportunities, make sharper decisions, and move faster as we push toward our goal of scaling aggressively in 2026.
It’s exciting and honestly humbling to realize that the businesses I started from scratch are now creating real jobs for real people. That responsibility isn’t lost on me. But it’s also one of the most rewarding parts of entrepreneurship: building something bigger than yourself and bringing others along for the journey.
This week’s win feels powerful because it’s not just about adding team members. It’s about building systems, creating momentum, and setting up the foundation to capitalize on everything we’ve been working toward.
2026 is going to be a massive year, and this is just the beginning.
💨 This Week’s Whiff: Delays, Deadlines, and Owning the Hard Stuff
Real estate has a way of humbling you at the exact moment you think things are finally lining up. And just like last week, the same deal that was supposed to close is now getting pushed even further out. We thought we were finally at the finish line, but once again, the buyer’s lender is moving at a snail’s pace because of the government backed loan program they are using.
More reviews, more paperwork, more waiting. It is the exact kind of slowdown everyone dreads, and because it is a government loan, everything takes twice as long as it should. So instead of celebrating a clean exit, we are dealing with another delay on a deal we have been ready to close for weeks.
Meanwhile, the loan on our end comes due in two weeks. If this thing does not land soon, we are likely looking at an extension. Not the end of the world, but definitely an unnecessary hit all because someone else cannot move with urgency.
That alone would have made this week feel like a whiff. But then there was a different kind of delay, one that falls squarely on me.
With Thanksgiving, travel, and family time (happy late Thanksgiving by the way), I did not complete my GoBundance One Sheet. It is supposed to be a full snapshot of where I am across all areas of life and where I want to go next. It is important work, and I let it slide.
Some delays are out of your control, like a slow moving bank wrapped up in government guidelines. But some delays are on you. And those are the ones that force you to look in the mirror. Holiday or not, I need to carve out space for the priorities that matter, especially when they are tied to who I am becoming.
So the One Sheet is getting done this week. No more pushing and no more excuses. It is okay to slip sometimes, but if you want to live an exceptional life, you have to take exceptional actions consistently, especially when it is not easy or comfortable.
This week’s whiff was a mix of external setbacks and internal accountability. Not fun, not glamorous, but real. And honestly, weeks like this are where the most growth happens.
Next week, we tighten up and execute.
🎯 Tactical Tip of the Week: Use Case Studies to Hire Smarter
When you are hiring for any role, especially in a small and growing company, interviews alone will not tell you what you need to know. A resume shows experience, and an interview shows personality, but a case study shows how someone actually thinks and works.
Before you schedule interviews, send candidates a simple case study or small assignment related to the role. It does not need to be complicated. Just give them a scenario they would face on the job and ask how they would handle it. For example, a deal analyst could underwrite a small sample property, and a social media manager could draft a quick content plan or reel outline.
Why this matters
• It shows you how they solve problems in real time
• It filters out people who are not serious about the role
• It gives you a preview of their work quality before you invest in long interviews
• It speeds up the hiring process because you enter the interview already understanding how they think
The truth is, you can save yourself a lot of bad hires and wasted hours by making candidates show their work early. A quick case study gives you a clear snapshot of their skill set and mindset long before you get into deeper conversations.
👉 Action Step
Create a simple one page case study for every position you hire for. Send it to candidates before the interview. If they cannot or will not complete it, they are not the right fit. If they crush it, you walk into the interview already knowing you are talking to someone who can deliver.
A good hire starts with a good process. A case study is one of the easiest ways to separate real talent from resumes that just look good.
🔦 FROM THE FIELD: Gratitude, Good Food, and Grounding Yourself
This week’s lesson did not come from a walkthrough, a contractor call, or a deal update. It came from taking a real break and driving up to New England to spend the week in Connecticut, Massachusetts, and Rhode Island with my family for Thanksgiving.
Real estate moves fast, entrepreneurship moves faster, and it is easy to convince yourself that you will catch up with friends and family when things calm down. But they never really do. This trip was a reminder that you have to be intentional about carving out time for the people who matter.
At the same time, taking time off does not mean abandoning the important tasks you need to follow through on. The real skill is creating balance by using your time extremely effectively. Make space for the people you love, but also carve out the moments needed to keep your goals moving forward. Both matter.
Being with family, laughing, eating way too much, and stepping away from the daily grind is not wasted time. It is fuel. It resets your mind, fills your cup, and gives you the energy to get back to work with clarity and momentum.
And yes, sweet potato casserole is still the GOAT. Debate someone else.
The field lesson this week is simple:
Be intentional. Invest in your relationships and invest in your goals. Balance comes from prioritizing both with purpose, not sacrificing one for the other.
🎤 FINAL WORD
This week was a reminder that building a life, a business, and a vision is never just one thing. It is juggling growth and setbacks, discipline and grace, ambition and real life. From hiring new team members, to navigating more closing delays, to balancing family time with responsibility, the theme was clear. Progress happens when you stay committed, even when the circumstances are not ideal.
Entrepreneurship is not about perfection. It is about momentum. Some weeks you fly, some weeks you grind, and some weeks you simply learn. But every part of the process matters. The wins move you forward, the whiffs sharpen you, and the reflections keep you grounded.
What you can control is how you show up. The effort you put in, the standards you set, and the consistency you keep. That is where the real separation happens.
Thanks for being here and following along as this journey continues to evolve. The foundation is getting stronger, the team is growing, and the vision is expanding. Plenty more ahead.
Thanks for reading,
