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#8 What Smart Operators Are Tracking in 2025 (That Most Aren't)

#8 What Smart Operators Are Tracking in 2025 (That Most Aren't)

From AI risks to financing blind spots, here’s what you need to know to protect your margins and grow smarter. Tactical insights for contractors, operators, and acquirers who want to win in 2025—without taking their eye off the ball.

Christopher Hoffmann
September 16, 2025 • Estimated Reading Time: 17 minutes

In Today’s Newsletter

Owning the outcome: Results are YOUR responsibility
Things you should do…
The Pantheon sessions that I will be attending
Navigating Family Business Succession Without Losing the Family
Don’t get burned: the 3 most important questions to ask before hiring an AI Call Center partner
The hidden metric killing your close rate
Favorite Tweets from the past week

All of your leadership problems. Solved with the right hire. Uncommon Elite.

My friend and former Army 160th pilot, Christian Ruf, is helping business owners build high-performing teams by placing special operations veterans - think Navy SEALS, Army Rangers, Green Berets - in senior operations roles inside of businesses like yours. Check out his business, Uncommon Elite, and let him know that Chris sent you.

What’s on my mind?

Own The Outcome… Even When It’s Hard

We’re entering what we call the shoulder season. The phones are quieter. The weather isn’t extreme enough to drive HVAC or plumbing demand.

Historically, this is when some companies hit cruise control—waiting for the next heat wave or cold snap to get back to work.

But that’s not how we operate.

At HB Solutions Group, we believe in building stability, not waiting for it. Our Home Protection Plan (HPP) memberships are a key piece of that strategy. They ensure steady work for our field professionals and help us serve customers proactively—rain or shine.

I want to recognize our Blue Sky team, who just launched their HPP program this summer and already have a strong list of new members onboard. That’s what happens when you focus on what you can control—progress follows.

This mindset reminds me of a book that’s influenced how I lead: Extreme Ownership by Jocko Willink. His message is simple, but powerful: Leaders take full responsibility for everything in their world. No excuses. No blaming the forecast, the phones, or the economy.

When something goes right, own it. When something goes wrong, own it even more.

That mindset has reshaped how I lead at work—and how I show up for my family and in my personal life. Full ownership creates urgency. It pushes you to adapt, to improve, and to grow.

We’re seeing that mindset in action right now in Nashville. When call volume slowed, they didn’t sit back. They took initiative—showing up at local events, handing out door hangers, building community connections, and driving cross-trade leads. They also sharpened their marketing efforts, evaluating what works and what doesn’t.

That’s Extreme Ownership in the field. And it’s powerful.

So here’s my challenge as we navigate shoulder season:

Don’t focus on the weather.
Don’t focus on what’s outside your control.
Focus on your effort, your preparation, and your execution.

Every one of us has the power to make an impact—whether it’s turning over a lead, delivering 5-star service, helping a teammate, or improving a small piece of the process.

When we all choose ownership, we don’t just survive shoulder season—we thrive through it.

Let’s own the outcome together.

— Chris H

Discussing what the future can look for for these students at Lift For Life Academy - what an impressive group of young people!

My friend - Tommy Mello - nailed it again this year. Freedom 2025 was a blast, and if you haven’t done so already, sign up for Freedom 2026. It sold out this year, and will certainly do so again next year.

Visiting Montreal for the St Louis CitySC match - and brought home a 2-0 win! Special thanks to the CitySC team and staff for letting us travel with them - what a gameday experience!

Fall is just around the corner… and I cannot wait. The cool weather out at the farm makes for some special weekends with family.

Things you should…

If you attend a lot of industry events but always come home wondering, “was it worth it”, you should take an intentional approach to filling your schedule with high-value engagements at these events: set-up meetings in advance, select the sessions most relevant to you, and go strike up conversation with someone you wouldn’t otherwise.
If 2025 is a challenging year for you and your performance is persistently poor, you should consider making tough choices around expense control to protect the financial health of your business; “right sizing” overhead is tough. But I see too many folks wait until it is too late...
If you don’t know what your financing approval rates are for your 3rd party financing vendors, you should. Period. I’ve seen as high as 90% and as low as 55%. Huge implications for your success.

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Technology Corner with ServiceTitan

What I’m Most Excited About This Week at Pantheon 2025

Learning, Scaling, and Building Better at Pantheon 2025

This week I’m headed to Anaheim for Pantheon 2025, ServiceTitan’s annual event for contractors who want to grow, lead, and innovate.

There’s a lot to be excited about—new tools, new connections, and new ideas—but what I’m most looking forward to is learning from operators, technologists, and investors who are shaping the future of our industry.

Here are the 5 sessions I’m most excited about—and why they matter to me (and hopefully to you too):

1. Roofing and Exteriors Tools in Action
Why I’m going: We recently added Ferguson Roofing to our portfolio, and this session is packed with practical tools to drive faster, smarter estimates while protecting margin. It’s all about creating a more efficient exteriors workflow from quote to close.

2. The Enterprise Roadmap: What’s Now and What’s Next
Why I’m going: As HB Solutions Group grows across multiple markets and brands, we need centralized control, secure systems, and scalable processes. I’m eager to see how ServiceTitan is evolving to support businesses like ours that are scaling fast—but don’t want to lose focus on quality and customer experience.

3. Blast Off With the Field Mobile App
Why I’m going: Our field professionals are the heartbeat of our company. The right tools make their jobs easier, reduce friction, and improve outcomes for customers. I want to see how this new mobile experience can support our techs—and where we need to prepare for rollout.

4. A Day in the Life of a Trades Company CFO
Why I’m going: I’ve said it before—purpose and performance are not mutually exclusive. This panel will highlight how financial leadership is evolving from pure reporting to strategic impact. I want to hear how top CFOs are navigating today’s challenges while investing for tomorrow.

5. Rising Stars: Young Guns of the Trades
Why I’m going: The future of our industry is being reshaped by new entrants—many with private equity capital and aggressive strategies. I want to understand how they’re thinking, what’s working, and how our model of long-term private ownership can continue to stand out.

I’ll be sharing insights and takeaways throughout the week—so keep an eye out.

If you’re attending Pantheon and want to connect, send me a note.

#grateful to have ServiceTitan sponsoring this section of TPLT; Pantheon 2025 will be held Sept 17-19 in Anaheim, CA.

CEO: Growth Mindset

Navigating Family Business Succession Without Losing the Family

There’s no handbook for passing the torch in a family business — especially when that business involves your father, your brother, and a shared legacy built over decades.

When we began planning the succession of our family business, I knew one thing for certain: no outcome was worth sacrificing the health of our family relationships. I wasn’t interested in “winning” a negotiation. I was committed to preserving trust, alignment, and mutual respect — no matter how hard the conversations got.

What made it work for us? Perspective and purpose.

In family business conversations, you're rarely just one thing. You’re wearing multiple hats — employee, shareholder, family member — and the context changes everything. A management meeting is different from a board discussion. A board discussion is different from dinner at mom’s house. Understanding which hat you or your family member is wearing in each moment is key to keeping dialogue productive and respectful.

More importantly, we agreed that the long-term health of the business came first. That meant sometimes de-prioritizing our own short-term economic interests in favor of reinvestment, team development, and operational excellence. That kind of alignment doesn’t happen overnight — it takes honest, ongoing dialogue.

My 5 Hard-Earned Lessons on Family Business Succession:

Transparency is non-negotiable.
Say the quiet part out loud. What are your goals? What role do you want? What matters most to you? Clarity early saves conflict later.
Have the tough conversations now.
Before there’s equity on the table. Before titles change. Before assumptions become resentments. If you’re avoiding a conversation, that’s a signal it probably needs to happen.
Use tools to make it easier.
I handed my dad a short case study on family business transitions as a way to open the dialogue. It sparked a great, low-pressure conversation among the three of us and gave us common language.
Involve all siblings — even those not in the business.
Just because a sibling isn’t taking over doesn’t mean they shouldn’t understand how and why decisions are being made. Transparency preserves trust — and keeps Thanksgiving dinner drama-free.
Fair isn’t always equal.
Ultimately, it’s up to the founder to define fairness. Equal division of assets or control isn’t always the best path forward — especially if only some family members are continuing the business. Open communication around this principle can help prevent future friction.

At HB Solutions Group, our commitment to long-term, purpose-driven private ownership starts at home. We believe people & profits both matter, and prioritize relationships over ego, and vision over short-term gain.

If you're a business owner looking to transition your life's work to a team that will care for it like family — we’d love to talk.

CyberNetic Labs - bringing powerful Agentic AI tools to the trades

Don’t Get Burned: The 3 Most Important Questions to Ask Before Hiring an AI Call Center Partner

Choosing the right AI call center partner isn’t just a tech decision—it’s a business-critical one. Get it right, and you’ll unlock faster response times, lower costs, and improved customer satisfaction. Get it wrong, and you could face lost revenue, angry customers, and a damaged brand.

With so many vendors promising the moon, how do you separate the serious operators from the smoke and mirrors? Here are the three questions you must ask before signing any contract:

1. How do your AI agent booking rates compare to human reps—specifically in our industry?

If a vendor can’t clearly show how their AI agents perform compared to trained human agents, that’s a red flag.

At HB Solutions Group, we’ve tested AI against third-party answering services and saw a significant performance lift—faster response times, fewer missed calls, and better outcomes for after-hours booking. The right AI partner should prove their performance in your exact industry—whether it's HVAC, plumbing, or electrical services—not just show generic success stats.

2. How are escalations handled—and what does the human-AI partnership actually look like?

AI agents are great at booking straightforward jobs, but not every call is simple. Complex customer questions, emotional distress, or unique situations require human intervention. Your AI partner should be able to show:

How they route escalations in real time
How they hand off to humans (without frustrating your customers)
How they continuously improve by learning from escalations

In our experience, the best partners use AI as a first response, not a final answer—automating routine calls while partnering with humans (when necessary) to deliver exceptional customer experience.

3. Let me talk to a raving fan—and someone who fired you.

Forget the sales pitch. Ask to speak with both ends of the customer spectrum:

A client who’s thrilled and scaled successfully using their AI solution
A former customer who walked away—and why

This one request will tell you more about the vendor’s real-world performance and customer service than any slide deck ever could.

If they hesitate, you’ve got your answer.

Final Thought:
The wrong AI partner won’t just cost you time and money—it will harm your reputation. But the right one can enhance your brand, reduce costs, and free your team to focus on what they do best.

Choose wisely.

#grateful to have Cybernetic Labs sponsor this section of TPLT

Consumer Financing¹

Keep An Eye on Your Approval Rates

In 2025, many contractors are rightfully focused on expanding their financing offerings—zero percent promos, low monthly payments, extended terms. It’s a competitive landscape, and your financing program can be the deciding factor between a customer saying “yes” or walking away.

But here’s the part that often gets overlooked: approval rates.

You might think you’ve partnered with the best financing provider because they offer the lowest rates or flashiest terms. But if only 30% of your customers are getting approved, is that partnership actually serving your business?

A good financing partner isn’t just about what’s on paper—it’s about how often that paper turns into real, approved deals.

Let’s break it down:

If you're closing 100 calls a month and 40 customers request financing, but only 12 get approved, you’re leaving serious revenue on the table.
Not to mention, your team may be spinning their wheels quoting promos that rarely translate into closed sales.
Even worse—your customer experience takes a hit when expectations are set but not met.

Here's the call to action for 2025:
Start tracking your financing approval rate as closely as you track your booking rate or close rate. Meet with your financing partner.

If you want your financing program to be a true growth lever—not just a talking point—you need to understand the full picture, not just the flashy numbers.

High-approval, well-structured financing options = more closed sales. Period.

Let’s be smart operators. Let’s be data-driven. Let’s make sure our partners are helping us win—not just checking a box.

#grateful to have GreenSky® Home Improvement sponsor this section of TPLT

¹ The views and opinions expressed here are owned by The Path Less Traveled and its author and may not reflect the views of GreenSky®

This Week’s Favorite Tweets

Friends of The Path Less Traveled

Who are the VENDORS that fuel our success?

MARKETING

Choosing a marketing agency that is both (1) competent and (2) CARES about your specific business is hard. Over the last 5 years, I have become great friends with the founder of RYNO Strategic Solutions, Chris Yano, and can say with confidence that his agency is among the few that I would trust with my own brands. If you are searching for a partner, send a note to Jeff Bowab at [email protected] and tell him that I sent you.

PAYROLL & HR

Inova Payroll & HR has been a partner to our companies for over 10 years. They have provided us with a payroll technology platform that has been able to keep pace with the demands of our fast-growing organization (now serving team members across 4 states). Inova’s platform works seamlessly with our CRM, ServiceTitan, and with our accounting back-end, Sage Intacct.

COACHING & TRAINING

If there is one organization - perhaps more than any other - that has fueled our growth over the last 10 years… that organization would be Nexstar Network. I like to say that Nexstar Network has built & refined a “process playbook” that touches on so many facets of our business. Don’t try and re-create the wheel… come and learn from the best. Reach out to my friend Kara Schuster at [email protected] and tell her that I sent you.

#grateful for the “Friends of TPLT” sponsors in this section

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