The Art of Holdings #2

CONCEPT
Right Deal, Right Team, Right Time

As the year winds down, many of us are focused on wrapping up projects or planning for the year ahead. It’s the perfect time to reflect on one of the most valuable lessons learned about closing deals.

Over the years, I’ve seen golden opportunities fall apart and seemingly bad deals turn into huge successes. It made me ask: what really makes a deal work? After much experience and reflection, I’ve boiled it down to three key variables that must align: right deal, right team, and right time. Whether you’re raising money, attracting investors, or selling a service, these three elements are essential to success.

Right Deal

Getting someone to part with their money—whether it’s for a seed round, a software purchase, or even a hot dog (unless they are very, very hungry)—is no small feat. People always weigh the opportunity cost of spending their finite resources. Why should they choose your offer over something else?

The Right Deal is about ensuring your value proposition and competitive edge make your offer irresistible. Keep in mind: people’s money isn’t sitting idle. It’s likely in savings, stocks, or other investments, earning at least a modest return. For them to invest in your business, they need to believe your opportunity will outperform simply sitting on their cash.

Questions to ask yourself:

• Is the ROI compelling enough to beat their current alternatives?

• How does this meet their specific needs or desires?

• What exactly are they gaining from the deal that makes it worth the risk?

If you can confidently address these concerns, you’re presenting a deal that stands out.

Right Team

The Right Team is about having the perfect mix of expertise, credibility, and alignment to execute on the opportunity. A solid team doesn’t just bring skills—they inspire confidence in investors, partners, and clients, that the project will succeed.

When evaluating whether you have the right team, consider these key questions:

• Do we have the skills and experience to deliver on the opportunity? Highlight team members who have tackled similar challenges or achieved notable successes.

• Does our team inspire trust? Credibility matters. A team with a strong reputation and track record can ease doubts and reduce friction in negotiations.

• Are we aligned on the vision? Everyone on the team should understand and buy into the goal of the deal, presenting a united front to external stakeholders.

Even the best ideas need a capable team to bring them to life. Stakeholders aren’t just betting on the deal—they’re betting on the people behind it.

Right Time

Timing is often the most critical and elusive element of a successful deal. Even the best ideas with the strongest teams can fail if the market isn’t ready. Having experienced both sides of timing—too early and just right—I’ve learned how much it can make or break a deal.

Ask yourself these questions:

• Is the market ready for this opportunity? Timing too early might require costly education, as I learned with my 2019 startup, Hilani. While our AI-powered chatbot idea was innovative, the market wasn’t yet familiar or comfortable with the technology, making it harder to gain traction. We were ultimately successful in raising capital and kicking the brand off, but it took longer than we anticipated because of the extra education the market required of us.

• Are there current trends or events we can leverage? Keep an eye on macro and micro trends. For example, during the early days of the pandemic, I saw opportunistic deals like hand sanitizer brands thrive because they capitalized on immediate changes in consumer and business behavior.

• Do we have the capacity to act now? Timing isn’t just about the market—it’s about whether your team and resources are ready. A founder I worked with in 2023 exemplified this by aligning every detail before launching their fundraising round, ensuring they could execute immediately.

Great timing can be planned, like waiting for the market to mature, or opportunistic, like seizing an unexpected opportunity. The key is to stay prepared and informed so you can strike when conditions are most favorable.

Challenge for you: Reflect on a deal you were involved in that didn’t quite come together. Was one of the three key elements—right deal, right team, or right time—out of alignment? Which one, and why? I’d love to hear your thoughts—reply and let me know!

What I’m into this Week

• Reading: Life Force by Tony Robbins. I picked up this book while recovering from the Jiu-Jitsu injury, and it’s been a powerful reminder of the importance of health. One quote that stuck with me: “A healthy person has a thousand wishes. A sick person only has one.” which is up at the top of this letter. It’s a sobering thought—if you feel good today, don’t take it for granted. You never know what tomorrow may bring.

• Tool: Vizcom - This incredible AI-powered design software was introduced to me by an old colleague, and I had the chance to meet some of the team behind it. Vizcom allows designers to iterate on their ideas faster, pushing their creativity further in less time. I’m excited about its potential to elevate the quality and creativity of consumer products—from clothing to cars. I even introduced it to my wife, Chelsey, who’s an interior designer, and she’s already using it to enhance her projects.

• Watching: Drumeo - I’m not a drummer, but I’m fascinated by masters of their craft. Watching a funk drummer cover a Tool song was inspiring—his ability to let go and enter a flow state was nothing short of mesmerizing. If you enjoy seeing people excel in their element and reaching peak flow state, this is worth checking out.

Opportunities for Collaboration

• E-commerce Operations: Do you have an e-commerce brand in your portfolio? At Best and Basic, my operations agency is helping brands tackle some of the biggest challenges they face: reducing shipping costs, managing 3PL relationships, handling RFPs, and optimizing operations through consulting and software development. Thanks to a strategic partnership with one of the largest carriers in the world, we’re helping brands secure 30–50% better pricing on shipping and fulfillment. If cutting costs is a priority for your brand, let’s connect.

• Real Estate: Many of you know that for the past few years, I’ve been spent a lot of time working remotely from Playa del Carmen, Mexico, and have witnessed firsthand the region’s incredible growth and opportunity - like the addition of a new airport in Tulum and the Tren Maya that connects the entire region via train. I’ve partnered with a local real estate firm to advise on investment opportunities in this booming market. If you’re curious about the potential in Playa del Carmen and the surrounding areas like Tulum, I’d love to discuss it with you.

• Professional Services: As a finance professional, I understand how critical and expensive it can be to build a solid finance infrastructure. One of my partners offers outsourced finance services to act as your finance department at a fraction of the cost of hiring in-house. Whether you’re looking to streamline processes or improve cash flow management, we’re here to help.

• Job Opportunity: My friends at Accel Health are hiring their first Business Development Representative to join their sales team. If you or someone you know—are interested in being part of a fast-growing company, reach out for more details!