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Owned by Caleb

Full stack coaching for home service owners. Customers, Production, Money, Team, Systems — the whole business, not one skill.

15 contributions to The Lion's Den
Ai and People in leadership
I find myself still resorting to asking people to do too much and ai to do too little. need to run more requests through a different filter
1 like • Oct 9
Any examples you can share?
personal AI agents are coming for your business...are you ready?
ChatGPT just released Dots. Meta has Muse. GrokBot and Perplexity Computer have been out for awhile. Anthropic is no doubt on the verge of releasing something similar, as is Google. OpenClaw was huge and then it wasn't (that took about 60 days lol). Hermes is having a moment but is probably weeks away from obsolescence. This technology is rapidly iterating from early adopter status to widespread adoption, and I think it will happen a LOT faster than cellphones and the internet. We are facing a reality where it's not unrealistic to think that within a year, most tech savvy customers will have their personal AI agent deal with you. In two years, your grandma will have an agent. So the big question for us home service owners is, what are we doing to prepare for that eventuality? Here's what I'm doing... I'm thinking about what the workflow will look like from the client's side, and how I can make our business the most obvious one for their agent to interface with. I'm thinking about how the customer experience will change- how and where the human touch will still be relevant or necessary and what we will do to enhance those increasingly rare opportunities to get the most out of them. I'm thinking about how I can position my business now to be best prepared for a new way of doing business with people who now no longer need to pick up the phone, search the internet, book an appointment for themselves, or shop for themselves. It's coming, I have no doubt. Now's the time to be thinking and preparing for it...
personal AI agents are coming for your business...are you ready?
0 likes • Oct 9
@Nathan Aichele it's very cool, but i think it will always be a niche product. too complicated for the average consumer. especially when the big players are commodtizing agents rapidly. They will be ubiquitous soon.
0 likes • Oct 9
@Nathan Aichele curious how you are handling security with these agents? Like what do you have in place to protect against rogue agent instruction injection? stuff like invisible instructions hidden in emails using white text or tiny fonts, stuff like that?
Va
What’s the average cost to hire a Va to take inbound leads and set up estimating appointments?
1 like • Oct 9
My Executive Assistant makes $1600/month and is basically on call. She doesn't really have a clear set of expectations every day. I deploy her on projects as needed. Sometimes she's slammed, sometimes there's not much to do. If she lived in the states and worked as a full time EA for a C suite level exec she'd probably be a 75k-85k/year level employee.
Help me shape Thursday's call
Quick one, I need your input before I change anything. Thursday's call has been open Q&A with me. Right now it's locked to VIPs. I've been thinking about turning it into structured sales training, where we role play and work through real calls together. But I don't want to swap out something that's working just because I like the idea. So vote below. If you'd pick a second meeting, drop the day and time that actually works for you. If you feel strongly either way, message me directly. I want to hear it. And honestly, thank you for being in here early. You're the ones helping shape what the Den becomes. What's the one sales problem you'd want us to hit first?
Poll
9 members have voted
3 likes • Oct 5
@Jon Karmazyn we have our CSRs handle scheduling now. there used to be a handoff to a dispatcher, but it slowed the process down and created leaks in the bucket. now, whoever gets assigned the lead owns it from start to finish. that includes all follow up, closing the job, scheduling, re-engagement post sale, etc. i wanted a sense of ownership across the entire customer experience, since that aligns with one of our core values (extreme ownership: we own our jobs, our schedules, our clients, our roles).
1 like • Oct 5
@Kris Cook yeah that's totally fair and I see the other side of it. It's something we've gone round and round about. Ideally we'd have a clean "assist" process so that warm prospects who are ready to move don't have to wait too long for their account managers to re-engage.
Do you have a Sales "Bible"?
@Kris Cook has been talking a lot about sales playbooks and setting reps up for success. I figured I'd chime in. I see this as three disciplines: 1)education 2)process 3)repetitions Here's how I handle item #1- education. I prepared a comprehensive sales guide for our reps. This combines several elements into one sales reference that reps can repeatedly turn to when they need it. Inside, they can find... - technical info about our services (the "what we do and how") - value propositions for each service (common emotional needs that drive prospects to request each service and how we can meet those needs) - strategies for establishing rapport, building value and gaining trust - common objections and how to overcome them This is not just a training resource for new sales reps...it's their sales "bible" and source of truth for selling in a way that aligns with our USP and UVP. If you don't have something like this yet, it's a great project to work on. If you plan to delegate sales to someone else at some point, this is one of your highest leverage internal assets, imho.
Do you have a Sales "Bible"?
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Caleb Wininger
3
17 points to level up
@caleb-wininger-7805
I help home service business owners grow their profit & freedom. 5000+ hours of coaching experience. 25+ years as a 7-figure home service operator.

Active 3d ago
Joined Sep 27, 2026
INTP
Detroit, MI
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