Yacht Workshop: How To Scale Without Becoming A Slave To Your Business| E519

Summary

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Podcast Summary: The Rich Somers Report

Episode: Yacht Workshop: How To Scale Without Becoming A Slave To Your Business (E519)
Host: Rich Somers
Guests: Danielle (Hotel Project Manager & Developer), [unidentified male and female panelists]
Release Date: June 25, 2026

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Main Theme

This episode centers on how business owners and entrepreneurs can scale their companies aggressively—without becoming a slave to their own business. The discussion dives into time management, delegation, team-building, and maximizing productivity, all tailored through a real-estate and hospitality lens. The panel engages in a candid, tactical group coaching session, drawing on their own business experiences to dissect bottlenecks and share solutions for sustainably scaling up.

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Key Discussion Points & Insights

1. Stepping Back to Identify High-Value Work (00:37)

• Rich Somers and panelists open by stressing the value of stepping back from daily operations to gauge team performance.
• Rich recounts a recent experiment:
  • "I told the whole team, I said, hey, I'm going to be hands off for the next month. ... There’s a lot of things that I was doing, and I thought I had to be doing them, and now ... they’re actually performing better ... It feels good." (B, 00:37)

2. The Challenge of Scaling While Staying Involved (01:14)

• Danielle voices a dilemma: she wants to scale but loves working in the business, especially design and strategy. She fears that scaling means being "stuck" just managing and training others.
• Key question: Can you scale without having to be the sole leader or constantly train/monitor a team?

3. Identifying Time Sinks & Energy Drains (02:28 – 05:39)

• Danielle lists:
  • Meetings (10+ hours/week, many for creative direction; they’re draining)
  • Permitting/admin work (5–10 hrs/week; a major time sink, not her best use)
  • Business development/lead gen (dislikes outreach/follow-up, enjoys in-person interaction but not emailing)
• Rich walks her through isolating these "energy drain" areas to see where delegation is possible.

Notable Quote:
"Do you ultimately really, really dislike lead gen and networking with clients? Because you seem pretty good at it."
— Rich Somers (B, 06:27)

4. Delegation & Systems: Freeing Time for High-Impact Work (07:13 – 12:27)

• Delegating Email and Permitting:
  • Rich strongly recommends hiring an assistant (EA) to filter and triage emails, and to offload permitting—freeing up creative or strategic time.
  • Suggests using video (Loom) walkthroughs to train assistants, setting up clear KPIs for follow-up.
  • "A lot of that is just very like, a lot of just like processes. ... Film a couple loom videos and show them exactly like A to Z how to do it and then watch them go do it and then cut them loose." (B, 07:15)
• Audit and Batch Communication:
  • Time-blocking and email triage; recognize most messages don’t need immediate responses.
  • "A lot, like 80% of this stuff is just distractions. ... I would never get anything done." (B, 08:59)
• Protecting Deep Work:
  • Time block key hours (especially mornings) for focused work, and cluster meetings to other periods.

5. Using Tech & AI for Productivity (12:27 – 14:30)

• Panelist D shares an in-development “inbox triage” AI agent:
  • It ranks incoming emails, flags urgencies, and drafts replies, further minimizing daily distractions.
  • Integrations with Slack (and eventual plans for iMessage) are discussed.
  • "Speed of communication, speed of communication. Let's go." (D, 13:27)
• Danielle notes using Notion’s AI features to summarize her inbox daily and prioritize tasks, although her role still requires her unique judgement for project-specific problem-solving.

6. Overcoming Control Issues & Perfectionism (17:01 – 18:21)

• Both Danielle and Rich admit to struggling with letting go due to perfectionist tendencies.
• Rich:
  • "I have such competent team members... And Alex and Lauren ... they’re like, like, you’re very hands on. I’m like, damn. Really? ... It’s because I’m a perfectionist. I want everything to be done right.” (B, 17:07)
• His recent hands-off experiment showed that things often improve when leaders stop micromanaging, though some areas may need occasional oversight.

7. Practical Tips for Batching, Scheduling, and Protecting Time (14:30 – 20:01)

• Batching Invoices/Financial Tasks:
  • Instead of ad-hoc invoice review, Somers’ team now only handles invoices on set days (15th/30th of the month), freeing mental space for the rest of the period.
• Setting Communication Boundaries:
  • Somers recommends restricting outreach to Mondays/Wednesdays after noon, and to vigorously protect mornings for strategic work.
  • Fridays are best for calls and networking; "people are in a good mood ... best time to get ahold of people." (B, 19:15)
• Time-blocking for content creation (Danielle):
  • "Wednesdays are my no meeting day. ... That's when I batch content." (C, 16:23)

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Notable Quotes & Memorable Moments

• Stepping Away to Test the Team:
  “There’s a lot of things that I was doing, and I thought I had to be doing them, and now … they’re actually performing better.”
  – Rich Somers (B, 00:37)

• Systematizing Email Management:
  "I would look to hire an assistant that you can delegate your emails to, and that’s gonna free up a lot of your time. ... Delegate that right out the gate, delegate the permitting process."
  – Rich Somers (B, 07:15)

• On Emails as Distraction:
  "If all I did, Danielle, was literally just like, read all these emails and text messages and like social media DMs ... I would never get anything done."
  – Rich Somers (B, 08:59)

• AI for Email and Communication:
  "My wife’s gonna be getting like AI messages, responses from me. … She wants to know like what I want for dinner. It’s gonna be buffalo chicken!"
  – Panelist D (13:27)

• Letting Go of Perfectionism:
  "It’s because I’m a perfectionist. I want, I want everything to be done right. And if it’s not done right, I’m like, no ... But it can like, work against you too."
  – Rich Somers (B, 17:07)

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Important Timestamps

• 00:37 – Rich discusses stepping back from daily operations
• 01:14–05:39 – Danielle’s struggle to scale without giving up creative/project work; Rich guides time audit
• 07:13–08:38 – Delegating admin work & effective email management techniques
• 12:27 – Panelist D details new AI email triage tool for entrepreneurs
• 14:30–16:23 – Batching invoices and protecting “deep work” mornings; Danielle’s no-meeting/content day
• 17:01–18:21 – Letting go of control, perfectionism, and seeing team thrive
• 19:14–20:01 – When to do calls, networking, and the science of batching communication for response rates

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Actionable Takeaways

• Time Audit: Regularly review your schedule to pinpoint tasks you can delegate.
• Delegate Repetitive Tasks: Use assistants (human or AI) for inbox management, permit processing, and admin work.
• Batch Processes: Group administrative tasks to minimize context-switching and free up creative/strategic energy.
• Protect Deep Work Blocks: Schedule meetings for afternoons or batch days; shield mornings for essential decision-making or creative work.
• Let Go to Grow: Trust competent team members with responsibility—even if you’re a perfectionist.
• Use Tech Tools: AI agents and productivity tools can help triage communications and maintain focus.

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For business owners and real estate professionals, this episode offers an engaging, real-world look at how (and why) to ruthlessly prioritize, delegate, and scale while staying out of the “slave to your business” trap.

Transcript

[A]

Hey, guys. We are buying two more boutique hotels along the California coast here with summer's capital. 45 rooms off market in Catalina island and a second deal up in Bodega Bay, which will make a total of eight boutique hotels owned and operated, our investors get passive income tax benefits. And the best part is, unlike investing on Wall street and a lot of these other asset classes, like multifamily, our investors get to go and stay and experience these boutique hotels firsthand to see how their money's working for them. And so if you want to learn to see if we can help you before this opportunity fills up, you can go to summerscapital.com invest to book a call with my team. [e-mail] invest to book a free call with my team. Now let's jump into the show.

[B]

I had to tell myself three weeks ago, I told the whole team, I said, hey, I'm going to be hands off for the next month. And it's good test to see how everything performs so I could focus on raising capital. And. And so I've been pretty hands off. And that's. That's been nice. And there's a lot of things that I was doing, and I thought I had to be doing them, and now I'm like, I'm not doing it. I'm like, they're actually performing better now that I'm not doing it. So I'm like, oh, my gosh, it feels good, you know, and so. And there's some things where I'm like, okay, I take my eyes off it, and it's not performing as good. And so. But it's good to kind of, like, analyze to see where you are, if you would, and just step back for a little bit.

[C]

I have a question for Rich, because what if you can't isolate your schedule like you do? Like, I. I'm kind of like a freak about my schedule. I'm a big planner. Like, my job is planning everything. But, like, what if you're always kind of on demand for clients? And I kind of. And I guess I'm like, thinking of my question as I'm asking this, but I work in my business a lot, but that's because I love it, right? And so it's like, I'm kind of in a place, and maybe I'll restructure my question about wanting to scale back again my business because I used to have four employees full time and how, like, I like working on the project. So I always find it difficult to scale if I don't want to If I still want to be working on hotels and. And being kind of like that creative director for the hotel development projects while still kind of growing a team and not getting stuck training everyone and kind of teaching them the process. Like, is it possible to scale without always having to lead a team? I guess. Is that a valid question?

[B]

So let me ask you this.

[C]

Okay.

[B]

So where are you spending the majority of your time throughout a given work week? Right now in meetings.

[C]

And that's kind of like where the first question came. Like, my projects are very detailed, and we have. I'm in like, 10 hours a week on meetings, and they happen throughout the week, and they're not. I tried to isolate them, but I'm not the only person on them.

[B]

Do you guys walk into every meeting with an agenda?

[C]

Yeah, we do.

[D]

Yeah.

[B]

Clear. Clear written agenda everyone has. These are the bullet points we're going

[C]

to cover by the designers. Yeah. And so. So I'm really. A lot of my time is listening to people in the meetings or kind of clarifying direction. But the designers and the architects are really the ones that are. There are a lot of, like, brainstorming meetings, but it does. It like, drains you.

[B]

And what are you doing with the other 30 hours in a week?

[C]

I'm reviewing stuff, planning stuff, like, for this hotel project that I have, like, a lot of it is just reviewing and studying and organizing and analyzing. So it's like you have that, like, cognitive analysis schedule, and then you're kind of listening to people, too. So I. I find that to be like, the hardest part of my schedule is like, the both.

[B]

Okay. And what would you say is your highest and best use of your time within the business?

[C]

Being on those calls, really? And the strategy that I'm doing, I think there's a lot of time. And this is kind of where I see as, like, my next hire would be, is with all the permit expediting that I do and kind of like the back end of it of like, organizing and tracking and filling out applications and making sure that things are getting included in the packages and.

[B]

Yeah, and then what. What arm of the. I guess, what area of where you spend your 40 hours do you feel like you like the least? Where it's not the best use of

[C]

your time filling out applications.

[B]

And how many hours a week do you spend doing that?

[C]

I'd say I'm on, like, five to ten hours a week doing that.

[B]

And then what's the. What's the next thing that you're like, hey, I don't love doing this, and you're spending a little bit of time

[C]

on the business development.

[B]

Business development. And what does that mean?

[C]

Outreach. Like LinkedIn.

[B]

Okay. Lead gen target. You don't like that part?

[C]

I like meeting them. I think it's like getting like studying target clients and kind of like the follow up via email is like, I hate it.

[B]

Okay. Okay. And the ultimate goal for you is to. You want to, you want to grow more top line revenue, you want to bring on more, more projects, more clients or do you want to like, what's the goal for you?

[C]

Yeah, I want to bring on more clients.

[B]

Yeah.

[C]

And more projects. And more high level projects. Right. Like I definitely target more luxury development. Right. And so like I'm trying to, I think up until this point I've done a lot of like select service hotels and now I'm targeting more high end and luxury. And so that's what I want to spend more of my time doing. And I like being involved in the

[B]

projects and so you like working in the projects? The design? Yeah, Seeing them come to life. Okay. Yeah. But you don't, you don't like the legion.

[C]

I don't like the legion.

[B]

And you don't like the permitting process.

[C]

Yeah.

[B]

Okay. Do you have someone good on your team? Do you have someone good on your team that is great at the lead gen and good at bringing in new clients?

[C]

I've downsized to myself and now an ea and like I'm at the point like, is my ea, do I train my EA to do this stuff or do I bring someone in that knows it? And I'm kind of like torn between.

[B]

Yeah, that. So my question to you is because I asked you what your highest and best use is within the business and you said it's working in the design element and with inside the business. Yeah, designing. However, do you ultimately really, really dislike Legion and networking with clients? Because you seem pretty good at it.

[C]

Thank you.

[B]

You were just talking to me about a potential hotel in Catalina downstairs. So do you not, do you dislike it? Like you're like, hey, like there's no way in fuck I'm going to do this?

[C]

No, I, I think it's like, it's the email side of it, you know, like I'm in. I get hundreds of emails on the projects a day. So like having to outreach to someone via email, I don't like, I love like meeting them. And so that's the easy part. I think getting to that is always like, I don't do it enough. And I'm like, oh shoot, I need to reach out to this guy Ken, because he just hired the GM that I referred him to. And, you know, I got to remind him about me, you know, like, that's the part I don't like.

[B]

So is there someone that helps you with your emails right now or the permitting on your team?

[C]

No.

[B]

Is there someone that could do it?

[C]

Yeah, I guess that's kind of. I'm like, at that point, it's like, who could do it?

[B]

So. So I would look to hire an assistant that you can delegate your emails to, and that's gonna free up a lot of your time. Okay. And then they just star. They just star at the end of every single day or throughout the day. The most important emails, if it's an emergency, they can bring it to you right away. And then when you get in the office in the morning, you can just review the start emails that are very important you can respond to. Other than that, they can respond on your behalf. I'm not in my emails a whole lot, but Lauren's in my emails and Alex is in my emails. And they just. Yeah, they just handle all my. If it's an emergency, if it's important, they start and I'll review it. A lot of the stuff I review, like, maybe once every two or three days and that's it. Now for the permitting process, that assistant or whoever you hire, train them on how to do the permitting process. A lot of that is just very like, a lot of just like processes. And so you can like literally just like film a couple loom videos and show them exactly like A to Z how to do it and then watch them go do it and then cut them loose. And then you can just track that as a KPI once a week when you meet. And then I would allocate all that time. How many, how many hours you said is 10 hours a week for permitting?

[C]

Yeah.

[B]

And how many hours would you say a week that you're going through emails in our.5.

[C]

My whole job is in emails. That's the problem.

[B]

So how many hours is in the emails?

[C]

Like four to 50 hours.

[B]

Okay.

[C]

No, I'm like, I. My. Every day there's like 30 issues that arise on a project in my email. And that's like, it does take a lot of time. And I've. I've tried using AI to help kind of automate and, and clean things up because, like, my notion communicates to my Gmail, which I love. So I'm working on that.

[B]

When you guys are just getting blown up in all these emails. And like, sometimes I Open my phone. I'm like, social media, my email and all this, people are texting me, you know, and as you grow a bigger, bigger thing, there's going to be lawsuits and all this stuff, right? We got lawsuits at the hotels. Guests, guests cut their finger or slipped in the pool and there's lawsuits. But, like, a lot of, a lot of that is just distractions. It's just smoking beers. And so you need to get clear out of all these emails, which ones are like, hey, these are like, really important that I need to like, respond to right away. And which ones can literally wait till next week on Monday. And a lot of it, a lot, like 80 of this stuff is just distractions. If all I did, Danielle, was literally just like, read all these emails and text messages and like social media DMS that I get throughout a given, a given day, I would never get anything done. And so I have to like, just drown all this out and just focus on the one or two things every single day that's going to move the needle. And I would do an audit of all these emails. I guarantee you that not 100% of these emails that you're getting every single day need to be responded to or attended to right away. You said a lot of them are issues that are popping up. But I guarantee a lot of those issues can be left burning till Monday. And I would time block, like, hey, Monday, or maybe it's two days a week where it's like every Monday, every like Thursday, I'm going to time block like an hour or two just to go and read through all these emails and kind of address. But I would try to delegate a lot of that stuff to team members and I would try to hire someone that's competent enough to go and attack a lot of that stuff. Like, I fully trust Lauren to like, make decisions on my behalf and, and like, literally facilitate the next step and like do a lot of the stuff for me. And so I think you need to get clear on what that looks like because you can free up a lot of that time to reallocate on your highest and best use. For me, my highest and best use is like raising money, shooting content, making decisions and selling. That's my highest and best use within my company. Right. But it gets tricky. I was just telling Briar, like during the lunch break, it's like, you know, I was telling him as he grows as an entrepreneur, he's going to continue to face a lot of these same challenges. And it's like, you got all these different arms of the business, right? And there's always fire is burning. And so it's like you sometimes you got to pick the one fire and you're gonna let all these other fires burn in the background and you're gonna like, you're gonna solve this one problem, take that fire out and fix it and then you're gonna move on to these next fires and like you're gonna start working on this one and then this one's gonna slowly start burning again. That's just a game, right? And so for you, what I would recommend is I think the highest and best use of your time really is the design element and then the lead gen on the networking part, not the emails and the back and forth. That's more administrative stuff. I would, I would bring in an ea, delegate that right out the gate, delegate the permitting process. I would delegate. I'm sure there's a couple other things that you're doing that you shouldn't be doing. Delegate that stuff out and then double down on your highest and best use. And that's decision making. That's the design and that's the lead gen, the true lead gen that's going to actually make you more revenue.

[D]

Danielle for since you're in seven figure creator, I'm probably like six weeks away, but we're building is an inbox triage. We're basically like I got an AI agent in my email that ranks the importance of an email on a scale of 1 to 100. And then it ranks it on how confident it feels like in answering it. And it is. Then it'll ping me if it's extremely urgent and it won't ping me if it's not urgent. So I don't have to actually worry about me checking my email. It gets filtered and then it will draft a message. And so I go in and my email right now is just send, send, send, fix, send, send, send. I'm gonna roll it out seven finger crater. But it's probably like six weeks away. But that is done. And I connected to Slack too. I connected to Slack too. So like and my imessage. Yeah, imessage isn't done yet. But eventually I kind of feel terrible about this. My wife's gonna be getting like AI messages, responses from me. Oh, I think that's I speed. Speed of communication, speed of communication. Let's go. I gotta pick it up. She wants to know like what I want for dinner. It's gonna be buffalo chicken no matter what. Like it knows me. Like, let's just send it. Let's get, let's get going.

[C]

I did that with my notion AI agent for a while because notion really knows my tasks and what I do. Right. Like, and so I did that. I can't do the draft because my draft is like problem solving for projects. Right.

[D]

How much of it is repeated? Is it net new every single time it's new.

[C]

That's, you know, it's a very complicated project. Right. And so like that's what people pay me to do is I can't automate that. But that's okay. You know, it's like, it's part of the strategy. I get the information and I'm trying to find a way to like use AI to kind of like what I've done is like my notion agent will read all my emails and every morning tell me like the priorities. And so it does save me time. Yeah. So I've kind of built that. But yeah, I mean it's, it is. I mean I do, I probably should be better about not always looking at my inbox and kind of allocating like beginning mid, end of day instead of being.

[B]

Yeah. And sometimes that means you gotta like just close your email. I know, like close the fucking email, close the Instagram, close your text messages and like literally just like focus. And if that means you got to have a second phone where this is like your focus phone and it like, you know, doesn't have all distractions and then go do that. But the other thing I would suggest is like, you know, if you guys have like invoices and all this, like people trying to, you know, bill you for this and that, like, you know, just keeping up with that, it's a full time job. And so like what we did beginning of last year, kind of like we have, we have probably like, I don't know, like 300, 400 vendors we work with every single month across all the properties. And these are all third parties that we use for the software and all that. Everyone wants to get paid, everyone's trying to secure the bag, right. And I'm like, that's a full time job, just like collecting invoices, seeing who's paid. And so now we're just like, no, like we pay invoices on the 15th or 15th and 30th are due and then we pay it seven days later. So we just tell all of our vendors, submit your invoice by the 15th or 30th of every month and you'll get it in seven days and that's it. So it's like we just batch now. You know, and it's like the other 14 days of those, that, that period, we're not, we're not worried about it or focused on it. The other thing is all these people that are reaching out that want your time, tell them like, hey, it's going to be, it's got to be on Monday or maybe say it's, it's only Monday and Wednesday after 12 o'. Clock. And protect your morning from the time you wake up till afternoon. Like, I don't know about you, but for me, I like to protect my mornings. So if I have to take like a, a meeting that's important and I can't wait till Monday, I'll put on the calendar afternoon because morning, I love the morning time to like, that's where I feel freshest and I can really move the needle. And I like to be in control and like, I'll protect my calendar in the morning.

[C]

Yeah, it's good. I do like to isolate that. We're dealing with an architect in London and so the mornings are like the time that they can talk, but we do. Wednesdays are my no meeting day. And I always say I'm busy and that is when I've been planning to batch content and kind of I focus on the content. That's been something I've been pretty consistent with. So I'm happy with that. And yeah, the thing is, as a pm, I'm the middleman. I just like, everything that's happening on the project comes through my inbox, whether I need to do something about it or I just need to know it. And so part of my job is just reading it, you know, and so I just need to like, you're probably,

[B]

you're probably like a little bit of

[C]

a control freak about the information.

[B]

I am. And like, like I, I, about a month was like three weeks ago. We're getting into like acquisition mode and I'm like, I gotta go raise all this money I gotta do. And so I was like, I was like, I need to let go of a lot of this. I'm like, I have such competent team members and all this stuff and, and Alex and Lauren was telling me the other day in the office and I was like, they're like, like, you're very hands on. I'm like, damn. Really? Like, yeah, you're very hands on. And it's because I'm a perfectionist. I want, I want everything to be done right. And if it's not done right, I'm like, no, like we're gonna, we're gonna Fix it, blah, blah. But it can like, you know, it can work against you too. And so I had to tell myself three weeks ago, I told the whole team, I said, hey, I'm going to be hands off for the next month and it's a good test to see how everything performs so I could focus on raising capital. And, and so I've been pretty hands off and that's, that's been nice. And there's a lot of things that I was doing and I thought I had to be doing them and now I'm like, I'm not doing it. I'm like, they're actually performing better now that I'm not doing it. So I'm like, oh my gosh, it feels good, you know, and so, and there's some things where I'm like, okay, I take my eyes off and it's not performing as good and so, but it's good to kind of like analyze to see where you are, if you would and just step back for a little bit.

[C]

I liked your loom idea because I think for me, like I've never documented my training in the past and now that I have a new team, you know, I have to redo it. And so I think I'm almost like burned out by that. But I like that idea that it's just consistent and like this is a process and kind of doing better at documenting that.

[B]

And another good thing for you is, you know, if you're doing your lead gen, you know, if it's calling people, I know for, for all you guys, like networking and all that sort of stuff, what I like to do is, is leave Fridays for that because Friday mornings, successful people, you know, on Monday, Tuesday, they're, they're busy, they're putting out fires that you try to get a hold of me on a Monday, like good luck. And, and so when I'm making my calls to investors and stuff like that, just touch base. I do that on Friday morning.

[C]

Everyone responds to me on Friday.

[B]

People are, people are like, yeah, people are like in a good mood on Friday. They're like, they might be working a half day, they might be taking a three day weekend, they're going on a little vacation. Like people in a good mood on Fridays. And that's a great, the best, the best time to get a hold of people Friday, Friday mornings to about early, early afternoon on Fridays. Great time. The next best day I think is Thursday, Monday, Tuesday are not good. People are like stressed out, they're putting out fires. They don't, they don't want to talk on the phone. And so if you guys are doing lead gen, structure your week around that, knowing, hey, Friday is a great day to call up clients, free up your calendar on Friday and Monday, Tuesday, you should be stacked because that's, that's, that's going to be your lowest response rate if you're calling people.

[C]

Yeah.

[B]

You know what I mean?

[C]

That's helpful.