July 17, 2025

#217: Kelcey Lehrich (365 Holdings) — Building the Forever Home for E-Commerce Companies

Kelcey Lehrich is the Co-Founder and CEO of 365 Holdings, based in Akron, Ohio. 365 Holdings acquires and operates consumer products companies, with a focus on eCommerce and a goal of long-term ownership.

In our conversation, Kelcey shares his path to entrepreneurship and his evolution from making his first acquisition to becoming a seasoned operator. He weaves in lessons from challenging ventures, unconventional acquisitions, and the earned wisdom of building durable businesses in the competitive world of e-commerce.

We unpack how Kelcey thinks about demand creation versus demand capture, what it takes to build a resilient holding company, the tradeoffs between a centralized shared-services model and a decentralized structure, and how to create the best long-term home for brands. He also shares wisdom on what makes a company worth buying in the first place, lessons learned from organizing the HoldCo Conference — the un-conference of Micro Private Equity — here in Cleveland, and much more.

Kelcey offers valuable insight for anyone exploring entrepreneurship through acquisition — or simply curious about how to thoughtfully scale something of quality over time. Please enjoy!

00:00:00 - The Entrepreneurial Spirit Unlocked  
00:05:32 - Navigating Early Entrepreneurial Ventures  
00:08:28 - The Birth of 365 Holdings  
00:11:18 - E-Commerce Evolution and Insights  
00:14:36 - Acquisition Strategies and Lessons Learned  
00:17:37 - Understanding Distressed M&A  
00:20:13 - The Rise of Entrepreneurship Through Acquisition  
00:35:33 - Evolving Business Strategies  
00:38:30 - Defining Success in Business  
00:39:46 - Core Values and Company Culture  
00:40:58 - Raising the Quality Bar  
00:42:59 - The HoldCo Conference  
00:45:20 - The Mindset of a HoldCo Entrepreneur  
00:47:01 - Incentives and Profit Sharing  
00:49:30 - Inspirations and Aspirations  
00:50:16 - The Future of E-Commerce  
00:52:12 - Opportunistic Acquisitions  
00:53:19 - Building in Northeast Ohio  
00:55:00 - Hidden Gem

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LINKS:
https://365-holdings.com/
https://www.linkedin.com/in/kelceylehrich/


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Past guests include Justin Bibb (Mayor of Cleveland), Pat Conway (Great Lakes Brewing), Steve Potash (OverDrive), Umberto P. Fedeli (The Fedeli Group), Lila Mills (Signal Cleveland), Stewart Kohl (The Riverside Company), Mitch Kroll (Findaway — Acquired by Spotify), and over 200 other Cleveland Entrepreneurs.

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Transcript

Kelcey Lehrich [00:00:00]:
One thing that happens in a portfolio is you end up with portfolio effects. The distribution of outcomes is not equal. You'll have outliers to the up and to the downside. So you have this constant capital allocation problem of your own time and attention and certainly financial capital of what are we doing? How am I handling this group of businesses that I have? Which ones are growing, which ones have challenges? And so you get this very different week or month or year of entrepreneurial operating when you're balancing kind of capital allocation as your primary challenge versus the focus company entrepreneur who's just going to grow their one thing. They've got this one boulder to push up a hill. I'm pushing six of them, but I'm running back and forth to whichever one is rolling backwards the fastest to try to get to stop while some of them are just taking off like a rocket ship up the hill welcome to.

 

Jeffrey Stern [00:00:46]:
The Lay of the Land podcast where we are exploring what people are building in Cleveland and throughout Northeast Ohio. I am your host Jeffrey Stern and today I had the real pleasure of speaking with Kelly Kelsey Lehrek, co founder and CEO of 365 holdings based in Akron, Ohio. 365 acquires and operates consumer product companies with a focus on e commerce and a goal of long term ownership. In our conversation, Kelsey shares his path to entrepreneurship and evolution from his first acquisition to becoming a seasoned operator, weaving in lessons from challenging ventures along the way, unconventional acquisitions and the earned wisdom of building durable businesses in the competitive world of E commerce. We unpack how Kelsey thinks about demand creation versus demand capture and what it takes to build a durable holding company in the first place, the trade offs of a centralized shared services model and a decentralized holding company building the best long term home for brands, wisdom on what makes a company worth buying in the first place, and lessons learned from organizing the Holdco Conference, the unconference of Micro Private Equity here in Cleveland and a whole lot more. Kelsey is full of insight for anyone thinking about entrepreneurship through acquisition or is just curious about how to thoughtfully scale something of quality over time. So please enjoy this awesome conversation with Kelsey Lardick. Lay of the Land is brought to you and is proudly sponsored by Roundstone Insurance headquartered in Rocky River, Ohio.

 

Jeffrey Stern [00:02:19]:
Roundstone shares Lay of the Land's same passion for bold ideas and lasting impact from our community's entrepreneurs, innovators and leaders. Since 2005 Roundstone has pioneered a self funded captive health insurance model that delivers robust savings for small and medium sized businesses. They are part of the solution to rising healthcare costs, helping employers offer affordable, high quality care while driving job creation and economic growth throughout Northeast Ohio. Like many of the voices featured on Lay of the Land, including Roundstone's founder and CEO Mike Schroeder, Roundstone believes entrepreneurship, innovation and community to be the cornerstones of progress. To learn more about how Roundstone is transforming employee health benefits by empowering employers to save thousands in per employee per year healthcare costs, Please visit roundstone insurance.com Roundstone Insurance built for entrepreneurs backed by innovation Committed to Cleveland I think having.

 

Jeffrey Stern [00:03:17]:
Kind of reviewed a lot of, you know, your your work and other presentations of your own story, it sounds like you've been entrepreneurial your whole life. And I'm always curious about the origins of the enterprising spirit within people and would love to understand when you felt that was unlocked within yourself. When did you come to recognize it?

 

Kelcey Lehrich [00:03:45]:
If you were to look at any personality profiling or assessment tool, you'd probably say it was inevitable. But I distinctly remember sometimes, probably my sophomore year of college at a stint at Lakeland in Kirtland Hills, a professor mentioning two books that I went out and bought as a sophomore. So I was probably 19 or 20 years old. That's when I first read Rich Dad, Poor dad by Robert Kiyosaki and Multiple Streams of Income by David Allen. I was like this entrepreneurship stuff sounds great. I don't know why I would go get a job. I'm sure those books were helpful. Again, I think it was probably inevitable, given my personality, that I would make for a very bad employee in most organizations.

 

Kelcey Lehrich [00:04:30]:
But there are certainly some very obvious, very early routes with things I was interested in early on. After college. I never had an actual salary, job or career. I was bouncing around from different entrepreneurial things for quite some time until I found my footing. And yeah, it started early.

 

Jeffrey Stern [00:04:51]:
As you were finding your footing. How did some of those pre career, early career entrepreneurial wanderings kind of shape your allocat? What was your approach to trying to find your footing?

 

Kelcey Lehrich [00:05:05]:
I think I had just an incredibly high risk tolerance and willingness to work really hard for a while. So I didn't have a lot of fun in my 20s. My wife and I took like a real vacation until like our late 20s. Despite being married for quite some while some time I think I was just really committed to wanting to do my own thing and that kind of matched my risk tolerance and my willingness to put in just a lot of hours and I was going to figure it out.

 

Jeffrey Stern [00:05:32]:
Yeah, well where from that, you know, kind of marrying the tolerance for risk with the work ethic to just kind of figure it out. Did you arrive at the opportunity to acquire other companies? Like where does that kind of.

 

Kelcey Lehrich [00:05:50]:
Yes. In those, those early entrepreneurial journeys I had a stint in and around the franchising world. So I worked for some franchisors as an outsourced franchise salesperson. And so I kind of like the idea of helping people get into business for themselves and look at startup business plans in the franchising context. I ended up networking my way to an organization in town that was a business brokerage. So selling small businesses here regionally and I ended up buying the business brokerage from the business brokerage founder on an earnout.

 

Jeffrey Stern [00:06:22]:
Oh wow.

 

Kelcey Lehrich [00:06:23]:
Began brokering small companies. Don't think I made a lot of money doing that. I was probably very young and very naive, but I certainly gave it a run and sold a few deals over a few years. But I realized kind of quickly that as a business model, even the worst business that I sold was a better asset than the asset of owning a business brokerage. Revenue is incredibly lumpy, very hard to forecast demand, hard to scale, just lots of challenges. It's very boutique kind of consulting, little service business. And I quickly found myself wanting to get into other businesses. So my now partner today, he and I started buying small companies for thousands or tens of thousands of dollars, many times through seller notes or through friends and family money.

 

Kelcey Lehrich [00:07:08]:
And we just kind of started building a little collection of these little companies that individually were kind of just side hustles but together could scrap together a living for the two of us. With the overhead of a laptop and a cell phone.

 

Jeffrey Stern [00:07:20]:
How did you know how to do any of that?

 

Kelcey Lehrich [00:07:23]:
I don't know. I just figured it out. Yeah, I think selling and strategy and spreadsheets and basic business models just isn't a difficult thing for me personally. And again, I always had the risk tolerance and work ethic to kind of figure it out. So opportunity always was appealing and I was willing to go pursue it.

 

Jeffrey Stern [00:07:47]:
Did you have at that point with your partner a vision that 365 holdings might develop into this platform holding company or how are you approaching, I guess the. The day to day versus the long term strategy of it?

 

Kelcey Lehrich [00:08:05]:
Ironically, there's always an interest to do multiple things. We always had more than one thing going on. And for years people that you should focus, you should pick one thing and really go all in on it. And we've done the exact opposite of that and it's worked out pretty well for us. I Think, but E commerce was not an early part of that formula. But having a holding company or having a portfolio of businesses, probably back to that kind of early reading in college, you know, multiple streams of income and Robert Kiyosaki and some of those things. I think that was always interesting to me. Kind of the entrepreneur in town that had a lot of things going on that just seemed like a fun way to do things.

 

Kelcey Lehrich [00:08:43]:
I certainly have a low amount of patience and a hard time focusing and a lack of attention to detail. So of course, like pushing one boulder up a hill is not as much fun as pushing up six at one time. We should, we should push up six at one time. And here we are. It's worked out.

 

Jeffrey Stern [00:09:00]:
Okay, so at what point does 365 holdings come into existence? What's, what's kind of. How do you think about the founding and origins?

 

Kelcey Lehrich [00:09:09]:
Yeah, so Justin, my partner and I, we had assembled this little ragtag group of a half dozen or so little service businesses and we finally sold one for $100,000, which is just enough money to be a 10% down payment on a million dollar SBA loan. So I went shopping for a million dollar business. I ended up getting on every business broker's email list I could find, look at all kinds of things. Ended up finding an E commerce business that had a low multiple, a lot of cash flow, a small team and ready to sell, ready to exit owner. And between an SBA loan, our cash and a seller note, we had a deal made with that deal. We got a line of credit and we didn't take a whole lot of cash out of that business early on. So about 90 days after buying that company, we maxed the line of credit and took all the cash that we had generated in 90 days and went and bought another one with a seller note and kind of just over levered again. And I think at some point I was like, you know, we have these two E commerce businesses now.

 

Kelcey Lehrich [00:10:08]:
I'll do a couple million in revenue in the next 12 months. We probably should talk to our lawyer or attorney about some kind of holding company or structure to put on top of this. And there was a eight minute conversation that was like, I don't know, just pick some name. Nobody's ever going to see it. It's not like we'll have a website or anything. Just pick some numbers. And I'm like, okay, 365 days in a year. There was no thought to it of any kind and here we are.

 

Jeffrey Stern [00:10:33]:
Well, not to jump the gun as I. And more Interested ultimately in the journey than the destination. But how would you describe 365 holdings today? Just where the business is kind of set the stage a little bit.

 

Kelcey Lehrich [00:10:49]:
Yeah, quite different than that version one that I just talked about. Or even maybe the version 2 that was the scale up. The version 2 that was the scale up was really a thesis around brands that are very small, called a micro brand, needing the Internet as their primary means of distribution and the Internet enabling that, and there being a long tail of a high number of durably profitable consumer products businesses that were native to the Internet. The vision that we decided to scale up was to acquire these, run them pretty centralized, kind of a conglomerate business model and try to acquire as many as we could. This is a bit before the aggregator craze and had the Amazon FBA roll ups and stuff slightly before that. I have a friend down in Charlotte who had kind of gone this route. He inspired me to do this to a degree, but that's kind of version one. And as time played out we realized all the challenges with why that was not necessarily a great business model.

 

Kelcey Lehrich [00:11:54]:
So fast forward to where we are today and it's much more Pursuing a traditional decentralized holding company happens to be concentrated today in consumer products businesses. But the vision is really just to have a portfolio of independently owned and operated businesses under a common holding company. And our focus is less about is it a brand and is it E commerce and more about is it a really high quality business or not. So today I think we have a handful of high quality businesses. They all still happen to be in E commerce. I think as time goes by I'll look to diversify outside of consumer products and into other business models. What started as a vertically integrated conglomerate has quickly changed into a decentralized traditional holding company.

 

Jeffrey Stern [00:12:42]:
Realizing this may be a tall order, but just pulling on the E commerce thread, could you help set the stage for E commerce and how you came to understand it, how you've seen it evolve as a distribution channel over time, working with as many brands as you have who are utilizing it. What is E commerce exactly and what is your perspective on it?

 

Kelcey Lehrich [00:13:07]:
I think the reason I was interested in it was I saw my own purchasing patterns moving more and more online. I think my really quick and dirty the view of it today is there's essentially two ecosystems. There's an ecosystem of demand capture largely dominated by Amazon. So I have a thing I want, I need to go get it. I want it to show up in my door quickly. So I type it into Google Or Amazon or maybe here shortly chatgpt and I need this thing and I want to buy it. On the other end of the equation is demand creation businesses. These are classic businesses driven by advertising really unlocked through Facebook and Instagram and to a lesser degree now Snapchat or TikTok or other platforms.

 

Kelcey Lehrich [00:13:47]:
But places where you could interrupt a consumer and offer them a product they didn't know they wanted or needed, they decide they do want or need it, they come through a customer journey probably on your own website and buy something. Really it was the advent of social media advertising that really allowed that to be a thing. If you wanted to make the world's best organic peanut butter or a certain shoelaces made from vegan materials, I pick your obscure product category. You can now reach customers that wanted to hear about that thing thanks to social media advertising and storytelling on the Internet. And so I just thought there'd be many, many of these. I think there are. But the competitive dynamics within E commerce are just absolutely brutal and there's not a lot of excess returns on capital and particularly the big tech players, Amazon, Facebook, Google, et cetera are really good extracting all the economic rent out of that ecosystem. And so it's very hard to get a durable stream of cash flow out of those businesses if you are not going to run them kind of in founder mode.

 

Kelcey Lehrich [00:14:53]:
And by definition we're not running in founder mode, we're running in micro private equity business guy mode. We're going to go take this thing that somebody else started and see it onto this better future through scale, through a team, through shared services, through our experience. And a lot of those businesses really frankly don't survive the founder mode. They really need to be more owner operated. It's hard to institutionalize things like merchandising, product development, those are the hardest ones. It's easier to institutionalize customer service, advertising, web development, we're pretty good at that stuff. But it's hard to find businesses that we can acquire where the real soul of the brand products, the innovation, what customer needs we can meet, can really be done on a scalable basis. For most widgets you can just go to Alibaba and import one from China tomorrow and you're in business.

 

Kelcey Lehrich [00:15:40]:
So finding businesses for our perspective that really have a moat is really, really hard. That is one that we can both operate and is also worth paying for. And we're not going to have a disintermediation risk of somebody else coming in and just spinning it up tomorrow. So in the portfolio today, my favorite Businesses are the ones where we have really operationally intense supply chain. It's a really defensible business model because it'd be hard to just go compete with us tomorrow in the size of the market that we're in, competitive position that we have. We've got a pretty good business model to capture as much of that market share as we can. And it'd be hard to just compete with us tomorrow because of the supply chain and scaling up a new operation. So I think for us in consumer, the future is probably more of these niche products where we dominate a market.

 

Kelcey Lehrich [00:16:27]:
We own supply chain or we own manufacturing in some way because I think everything else largely ends up at a commoditized kind of Amazon type of product experience. And there's very, very few businesses that we can find that don't require us to be that founder kind of expert in that brand.

 

Jeffrey Stern [00:16:46]:
Lots of threads to pull on there. I think the one I'll pull for the moment is when you think about what makes for a good E commerce acquisition target for you, you kind of outlined this durable competitive advantage.

 

Kelcey Lehrich [00:17:06]:
Just strong brands today that only comes from two places. It's either the supply side or the demand side. So the supply side has got to be product development, manufacturing, supply chain operations. How do we make the thing? And you almost have to make it because if you're just ordering it from a factory, then anybody else can order it from a factory and slap a label on it. On the other end is the demand side. Advertising, content creation, storytelling. Being good at both is really what makes for a quality asset in our view, particularly if it's a transferable business where our team or a successor owner can still do both in a sustainable way. Those are the two components in my mind of like boiling down to the essence of a consumer product, business, supply, demand.

 

Kelcey Lehrich [00:17:47]:
How do we make the thing that nobody else can make and how do we market it in a way where we can be competitive?

 

Jeffrey Stern [00:17:55]:
How do you navigate the actual acquisition of the company and working with the founders who've maybe gotten it to where it is but aren't going to take it to where you believe it can be?

 

Kelcey Lehrich [00:18:09]:
That's my job, that's what I'm here for. I don't do a lot else anymore other than try to find new opportunities for the team. Yeah, we look at businesses that are listed publicly from brokers. We've done a number of turnaround deals for businesses where there's a good business model, but there's a balance sheet challenge. We've done lender foreclosure deals. We've done a few transactions helping people avoid bankruptcy and try to turn around these balance sheet challenges. But deal flow comes from a lot of different directions. Some of it comes inbound, some of it's again actively marketed by brokers or bankers.

 

Kelcey Lehrich [00:18:47]:
But I'm always looking for other brands that we can own and operate.

 

Jeffrey Stern [00:18:53]:
How would you say that you have gotten better through subsequent acquisitions? Like what are the earned lessons there? I have to imagine, you know, the first acquisition looks very different from the one year you're running today. How have you maybe formalized those lessons that would inform something like a playbook if you have something like that?

 

Kelcey Lehrich [00:19:18]:
Yeah. The team keeps asking for the playbook and I keep telling them I'm going to write it down, but I'm not going to because as soon as I do that, they don't need me anymore. I like to keep it up here. The bar for the standard of quality of what we judged to be a good business keeps rising. So I've seen a lot of things, made plenty of mistakes and acquisitions, lost money on all kinds of different deals, lots of different ways. Every chart goes up until the right until you own it and then it doesn't anymore. And I've just seen enough to know pretty quickly if it's a good quality asset for us. And the challenge has become I'm not finding as many of those businesses anymore as I'd like to own.

 

Kelcey Lehrich [00:19:59]:
And it's harder to find them. They're fewer and farther between last 12 to 18 months has been rough. Valuations are compressed, balance sheets are real messy. Seller expectations versus market prices for assets are really disjointed right now. So we've been doing mostly distressed, mostly balance sheet issue kind of transactions. Very few looks at things that are good, healthy, growing going concerns because there's not that many of them.

 

Jeffrey Stern [00:20:28]:
How do you kind of marry that with the focus on quality and kind of the durable competitive advantage?

 

Kelcey Lehrich [00:20:40]:
That's what we're looking for. And I think our lens of what meets those criteria just gets sharper and sharper. And what Kelsey of five years ago might have thought made for a good business is not what Kelsey of today thinks makes for a good business.

 

Jeffrey Stern [00:20:55]:
And is that due to changes in the dynamics of markets or due to your understanding of what makes for a good business?

 

Kelcey Lehrich [00:21:04]:
Some of both. I used to think that we would drastically improve most everything that we bought. We were smart, we had all these ideas, we're going to do all these things and now I largely think we'll be iterative we will not be revolutionary. So if you've never run Facebook ads, I'm probably not going to start doing it after I buy your business. It's probably a reason why you haven't done it. You're a founder, you're pretty smart, you've grown this asset. It is unlikely that that's a great idea of just volumes of untapped potential. I'm picking on Facebook ads.

 

Kelcey Lehrich [00:21:39]:
You can insert any tactic here, but by and large we're not going to come in and do something revolutionary. Might do something iterative, but probably not.

 

Jeffrey Stern [00:21:49]:
Revolutionary when you think about ameliorating these brands that you're bringing in house, what does the shared services kind of model look like? How do you parse the learnings of best practice across the portfolio and application to a new acquisition that comes onto the platform?

 

Kelcey Lehrich [00:22:10]:
We used to share lots of things. Used to be like a very conglomeratized, fully shared services model. Now looking more like a decentralized holding company. The only shared services is really executive management from the founders, hr, accounting and like true, it pushed down to the brands as all of their own ops and marketing, which again is kind of the core of what an E commerce business should be. So whether the brand is run by a leadership team or run by a general manager or CEO, that brand is responsible for its products, product development, its supply chain, its operations, its customer service. All those things getting product in and then all the marketing, sales and distribution, getting product back out the other side, whether that's on Amazon, direct to consumer wholesale, whatever those channels might be, none of that is shared. I think that we still have opinions from the holding company level of what we want to see happen as the vision for a business and what we think is a good framework for decision making. But those activities are executed at the portfolio company.

 

Kelcey Lehrich [00:23:14]:
There might be shared learnings or shared insights, but the work is done at the opco level.

 

Jeffrey Stern [00:23:20]:
So to the degree a company hasn't done Facebook marketing and maybe it doesn't make sense to as a consequence of that if it hasn't gotten them to where they are. I'm curious how you think more just holistically about Omnichannel. Right. If a lot of these are E commerce as the distribution channel at the highest level, how you think about what it looks like between dtc, Amazon, Shopify as a platform? You know there's like a lot to unpack there, but the different channels.

 

Kelcey Lehrich [00:23:54]:
Most product categories have certain DNA around how customers buy them. The first biggest fork in the road is whether the product is Bought or sold. If it's bought, you're capturing demand. Customers go looking for it. If it's sold, you're creating demand and you need to tell customers that they want it, Interrupt them with advertising, convince them to buy it. That's the first like big fork in the road within demand capture. You've got Amazon and Google as your primary digital channels. You got shelf space as your kind of real world channel and demand creation.

 

Kelcey Lehrich [00:24:33]:
It's content marketing, Facebook advertising, podcasts, those kind of things. Less so a play on Omnichannel unless you've reached some real scale and there's some real brand awareness. If you're talking about running super bowl ads and stuff, cool. You're big enough that you can have pop up retail and you can be on the shelves at Target and that kind of stuff, but you're at a different scale. There's for a small business, 1 to 50 million of revenue that's selling a consumer good. You're very, very, very likely either demand capture or demand creation. If you're demand capture, you probably can't do demand creation. If you are demand creation, you likely have a limited amount of demand capture.

 

Kelcey Lehrich [00:25:13]:
So easy example, I'm wearing a button down dress shirt, as are you. You and I might go looking for men's button down dress shirts and find a million people selling them. Or you and I can get an ad of somebody that kind of looks like us that says it's the stretchy one and I bought it because I'm going on this vacation and like you and I decide as young guys that we need to buy a new men's button down dress shirt. There's a certain limit of how many dress shirts get sold in a year. There's a competitive dynamic of how many people go looking for them. And following that demand capture bucket of I'm going to search for it versus how many people are sold them through demand creation of a new size, new style, new fabric, making somebody decide they want to buy something. But those are really kind of the two buckets. I think about everything through that lens of is it bought or sold? Is it demand capture, demand creation.

 

Kelcey Lehrich [00:25:58]:
And that really kind of fixes your total addressable market for that consumer product category. Shy of being Elon Musk and inventing flying cars, which is a whole new market, which is not what we're talking about today, the vast majority of consumer products fall into these known markets that have known sizes and known dynamics for how they're bought or sold.

 

Jeffrey Stern [00:26:19]:
Yeah. In the spirit of this demand capture versus demand Creation framework. Are there other frameworks that you have as kind of guiding philosophies to how you think about the business?

 

Kelcey Lehrich [00:26:34]:
That's definitely the biggest one. I think the other one that's helpful is when you get to a business of some good age, 4, 5, 6, 7 years old in E commerce we got like a long amount of history starting to really look at non subscription based businesses. So subscription sexy. If you can get somebody to auto ship every 30 days, it's great. That's a known thing. Let's leave that behind. Go back to the shirt idea. How often do people rebuy their shirts and what's the customer lifetime value and the cohorts and the repeat purchase rate and all this good stuff.

 

Kelcey Lehrich [00:27:07]:
I'm not saying that from the perspective of we're going to build this CAC LTV model and go raise a bunch of venture money and go public because we'll eventually get paid back. I'm not saying it in that regard. What I am saying is buying an older consumer products business probably means you've got a big customer file. You probably can do marketing and product development activities, emails, sms, product releases to reactivate your existing customer base. They're not totally lapsed. They will buy this season's new dress shirt. That's not really a venture scale game. If I can go in the hole and lose money for a long time to buy future profits, that's largely not a good idea.

 

Kelcey Lehrich [00:27:44]:
But I do think that it's underestimated how long you can wring value out of a customer base. We've seen this in some of the turnarounds we've done. But when there's an established brand name, there's established email, there's brand search, people looking for these products, there's a really good residual value of revenue from people who know about that business and it's a really more durable than I think most people would expect. If you've got any amount of repeat in the brand and any amount of longevity, 3, 4, 5, 6 years of doing good revenues. So that's important to us is length, length of time. I'd rather buy a 6 year old flat business than one that's just gotten on a rocket ship for three years, there's just more levers to pull on that older company.

 

Jeffrey Stern [00:28:29]:
What can you share about this distressed M and A experience that you've had? You know, if on one side and you were kind of starting with the strong balance sheet, the durable competitive advantage.

 

Kelcey Lehrich [00:28:40]:
We've been on both sides, we've had our own Balance sheet challenges for that's a longer story for a different podcast than today, but we've been on both sides of it. We've had issues. We've helped other people get out of their issues. From what we've learned at a very, very high level. If you're listening to this and you're a founder, CEO of some kind, you're running a business, the first thing I'd recommend everybody get really, really comfortable with is understanding their own capital stack what they're guaranteed on, who owns what in the business, what lenders are involved, and being very aware of what obligations you have if you take on, particularly debt financing. In today's world, it's really, really easy to plug in your Stripe account, your Shopify store, your Amazon account, your or even just your retail merchant services terminal that you have at like a local cafe and have somebody offer you money through your business. Hey, press this button, we're going to wire you money, you're going to pay it back over these terms. It's kind of wild how easily available that is.

 

Kelcey Lehrich [00:29:40]:
Another issue is like corporate cards are often personally guaranteed. What I tend to see, to answer your question, is a lot of people don't understand how their balance sheet works. In the event of distress, what are they personally guaranteed for if they can't meet all their obligations, what are the creditors that are going to be interacting with them? In what order? Who has senior priority? How do you negotiate through these things? It's a very, very tricky set of situations. Most people don't realize what they're on the hook for that's beyond balance sheet items. So we know we're on the hook for a personally guaranteed credit card. Founders don't often always know they're also personally liable for things like sales tax, remittance, trust taxes like FICA and FUTA payroll wages. There's a lot of personal risk that you have as a founder or executive in a business that might go past just what's obvious on the balance sheet. So certainly balance sheet workouts are their own art of getting everybody negotiated to a good outcome to save a company if it's savable.

 

Kelcey Lehrich [00:30:35]:
But if you're a founder or entrepreneur, understanding what your actual personal liability might be in a situation and how the different participants in the business and stakeholders are going to act is a whole interesting education that we've had the pleasure, slash unfortunate pleasure of learning in the last few years.

 

Jeffrey Stern [00:30:58]:
So you mentioned a little earlier on the kind of rise in what you might call popularity of just this strategy overall of entrepreneurship through Acquisition aggregators, roll ups, micro PE of some form or another might be a worthy detour to explore the Holdco conference in some capacity here. But I mean it's a topic that repeatedly comes up in conversation. I feel like I don't go a day or two without someone bringing up the demographic reality that you have this aging entrepreneurial boomer population for all these businesses across America that don't have a good succession plan in place and certainly overrepresented in places here like in Northeast Ohio relative to elsewhere. And really this kind of just growing awareness about what it is that you are doing actually and that it's a viable approach for some who might have this entrepreneurial been to them. But I'd love to just hear your thoughts on just kind of the industry from that side of things and how.

 

Kelcey Lehrich [00:32:15]:
It'S been So I think starting 10 plus years ago it wasn't a defined term. There was no ETA moniker. Being a search funder or something wasn't really an idea, at least not that you could easily find information on. Whereas today I would fully agree. Whether it's HBR's guide to buying a small business, books like Buy, then Build. You go on LinkedIn or Twitter and you see influencers and gurus selling courses and information on it. It's very trendy and sexy and entrepreneurship.

 

Jeffrey Stern [00:32:48]:
And forgiving real mindshare. Yeah, yeah.

 

Kelcey Lehrich [00:32:51]:
And it's a real thing. There is a volume of businesses that need to transact. I think my couple comments on it would be the statistics are what they are. The businesses that exist need to transact or they'll go away. Just the reality of things. That said, this was happening before it was cool. Maybe the numbers have changed, maybe the size of the ecosystem is different, but this has always existed. It just wasn't maybe as defined as it is today for people approaching it.

 

Kelcey Lehrich [00:33:19]:
I do think that the definitions today that have been developed are helpful in that they grease the skids of getting a deal done. So if you go down the rabbit hole and learn everything there is to learn about self funded search, I'm going to get an SBA loan. I'm going to raise preferred capital. I'm going to buy 100% of a business using 80% leverage. 10% seller note. 10% equity injection is a very down the fairway. SBA acquisition play. There's a playbook.

 

Kelcey Lehrich [00:33:45]:
You should just follow that exact playbook. Likewise in funded search, I'm going to raise a search fund. We're going to have a two year search period. I'm going to Raise committed capital, those people get a step up in the new vehicle and we find an asset to buy. That's a playbook. And I'm giving a rookie kindergarten level summary of both of those playbooks. My advice would be, if somebody is approaching this from the outside, is pick a playbook and follow it. The thing that I think is most frustrating is I have people that contact me, friends, people I've met at events that try to color outside of the lines in a way that makes it hard for them to get a deal done.

 

Kelcey Lehrich [00:34:19]:
The reason why these frameworks have been developed of here's how capital participates in the transaction, here's how we raise the money, here's what the deal doc terms look like, here's how sellers behave, here's how buyers behave, here's kind of the guidelines of what a market deal looks like. The farther away you get from those, the less likely it is to close a deal. There's a reason why those norms have been developed and tend to work much like in venture. There's a set of norms that tend to work a C to Series A, etc. If you're in the Valley versus you're in the Midwest, if you're in SAS versus medical, like there's norms that people have come to expect in venture. There are norms in what is now search. And I think people understanding that and trying to really understand those norms and follow them will make their lives easier.

 

Jeffrey Stern [00:35:04]:
It is why I inquired earlier about to the degree you have a playbook, your own, and why it's interesting, I think that I would say we're an.

 

Kelcey Lehrich [00:35:12]:
Exception to that because we're very opportunistic. Yeah, we're very, very opportunistic. And I'm solving a different problem. So we've built something that works for us. And if I was starting today from scratch, I might have to approach that differently.

 

Jeffrey Stern [00:35:29]:
Yeah. What problem are you solving?

 

Kelcey Lehrich [00:35:33]:
That we get bored and need new businesses to buy.

 

Jeffrey Stern [00:35:38]:
Yeah. Well, so in light of that, as 365 holdings has evolved from more centralized, that shared model in the beginning to more decentralized, where ultimately at this point, do you see it going? Where would you like to take it?

 

Kelcey Lehrich [00:36:01]:
Over the years, we've bought north of 20 different businesses. Some we've sold, some we've shut down. We have six in the portfolio today. We sold one last year. I think what we're going to continue to do is sell whatever the bottom one on the list is and constantly try to reinvest that capital into the best opportunities we can find existing businesses or new ones and then we're going to continue to want to do special situations. So if we find a business that we think we can operate well, it's got a balance sheet problem. We're uniquely positioned to help that business turn around and live on. So we'll look for those opportunities because frankly, they're a good value for us as a buyer where we want to go with it.

 

Kelcey Lehrich [00:36:40]:
We want to just keep doing this. It's great to have a team that is really good at running these businesses and there's certainly no shortage of them out there. I think our goal is to continue to grow the holding company and we'll stick with that.

 

Jeffrey Stern [00:36:54]:
Yeah, yeah. The follow on would be what success looks like. And it's like, can you quell your interest in just acquiring new businesses? I don't know if it's a solvable problem.

 

Kelcey Lehrich [00:37:11]:
Yeah, I think that having fun building a business with a business partner who I respect and enjoy working with, with a team that we've watched kind of grow up and become a really high performing group has been super enjoyable. As much as it sounds maniacal to talk about buying businesses all the time, we mostly operate. We might get one or two deals done a year, we might go two years with nothing happening. And so we certainly work hard as an organization. But I'm not some greedy, money crazed, 80 hours a week slave driver that's only trying to buy the next company immediately tomorrow. I think that we built this business to create a lifestyle for our teams, for our families, for the community that we live and work in to create a great business. There's these brands that need a home and if our platform can be that home for them, then we like to buy them and give them a good long term home. We're not trying to make them go public tomorrow.

 

Kelcey Lehrich [00:38:07]:
We're not trying to grow them at a certain rate. We don't have to hit some kind of funding metric to make them achieve some outcome. We're trying to build a portfolio of these great brands. So I think running a great business without having to sell my soul to do it is really what the version of success is that we're moving forward with and that we're on track for and that we're enjoying and to add.

 

Jeffrey Stern [00:38:32]:
Even some additional color to that. I did read your annual letters to the degree that they were available online and I did enjoy them.

 

Kelcey Lehrich [00:38:42]:
They're out of print for a minute. We'll get back on that soon.

 

Jeffrey Stern [00:38:45]:
But I can tell perhaps that you've enjoyed writing those I just kind of could feel that from within them. But you did explicitly in one of them, lay out the values as you've identified them as important to the business as like four tenants of it, the team and culture. EQ over iq, Relentless execution. Winners keep score. I thought those were, those were pretty awesome. And I'd love to if you could just kind of walk us through those.

 

Kelcey Lehrich [00:39:17]:
Yeah, I think at some point every entrepreneur founder gets some meeting with an advisor and they're like, you really should have a vision and mission and values and stuff. And I think we heard that years ago. Yeah, it's fine. We'll get to that. Yes, at some point around. Yeah, around like 20 employees, we got to thinking it was actually important and we should solve that problem and we should think about it and come up with a real answer, not just the corporate America answer that's on the wall. And so we probably spent a better part of a year trying to make something that was real to us as founders and getting advice from people we really respected about it. So we did land on four.

 

Kelcey Lehrich [00:39:55]:
EQ over iq Winners keep score. Relentless execution and team and culture first. And they really just embodied the kind of business that Justin and I want to run. Back to your question about what does success mean? Success means running an organization and keeping with those four values. Those are the things that are important to us. We think it's more important the way you relate to your coworkers with a sense of self awareness than how smart you are. We think that we want to win a business. We need to track the numbers and be profitable and have accountability with what we're doing.

 

Kelcey Lehrich [00:40:23]:
We don't kill ourselves. We like to work hard and we enjoy relentlessly executing against the business plan. These are the things that we want to do every day, and that's why we picked them.

 

Jeffrey Stern [00:40:34]:
You've mentioned this idea of raising the bar for quality, almost a quality barometer, over time, both with, within and without, with regards to the team and with regards to the companies that you're acquiring. How do you raise your own quality barometer? What does that exercise look like?

 

Kelcey Lehrich [00:40:58]:
I think it's been lessons learned. We've seen business plans, we've made formal or informal projections or expectations about a deal or an initiative or a project or a product line. And it's easy as an entrepreneur to have a salesman's mentality, if I'm going to build this thing and everybody's going to love it, it's going to be great. And then reality sets in. That's not always the Case. And so I've gotten more discerning around the standards to which I expect things to work and the dose of reality that I apply to aspirations. The aspirations of growing a business, the aspirations of how profitable it should be, how likely the product line is to succeed. Whether people are going to be interested in this in six months or six years.

 

Kelcey Lehrich [00:41:50]:
Just really thinking hard about the durability of it, not about the ability to promote or sell or grow it necessarily. Those things are important. Like we need to drive the business forward, but having a bit more of a sober view to the quality of what we're doing and the value it drives to customers as opposed to the visionary sizzle that we can promote it with.

 

Jeffrey Stern [00:42:14]:
That makes a lot of. Makes a lot of sense. I like that a lot.

 

Kelcey Lehrich [00:42:17]:
And don't get me wrong, like every founder needs to like believe the dream and sell the vision. Like I totally get that asterisk. I try to be more conservative with that than not as time goes on to better set expectations and to get a more durable business model.

 

Jeffrey Stern [00:42:33]:
Yeah, it. I don't know why exactly, but if, if. Have you ever read the Art and Zen of Motorcycle Maintenance?

 

Kelcey Lehrich [00:42:41]:
I've heard of it. I've not read it there.

 

Jeffrey Stern [00:42:44]:
There's this whole bit that I was just reminded of as you were talking about that with regards to like quality and how it's. It's when things go wrong that you often get to pay attention to it. Tell us a little about the. The Holdco Conference.

 

Kelcey Lehrich [00:43:03]:
So I've got a friend in town, his name is John Wilson, runs a family founded home services business of like plumbing and H Vac and things like that. They're based in Akron and when time we met we had like similar number of portfolio companies, similar team size, even like similar revenue. Ish. And we'd met some other folks that were also building portfolios of disparate businesses, manufacturing software, whatever it might be. And looking around at various entrepreneurial ecosystems, we didn't find what we felt like was a community or event geared towards what we were doing at the time. And so John and I started the Holdco Conference. We ran it twice in Cleveland actually. Subsequently I exited that business and John's got a new partner in it.

 

Kelcey Lehrich [00:43:47]:
I went this year. I was at Sundance in Utah. Awesome. But it's really this event geared towards the Holdco entrepreneur. The person running more than two businesses, trying to scale multiple seven and eight figure businesses and grow them forwards. Nothing wrong with focusing on business. That's great. But if you have a software business, there's a software conference for you.

 

Kelcey Lehrich [00:44:08]:
If you have a software business and a trucking company and a medical billing business and an Amazon brand like there, it's hard to find a place to call home, except for maybe hold co conference because you'll probably find somebody there who has done some version of all of that before. And so it was just designed to uniquely address the challenges of small holding companies.

 

Jeffrey Stern [00:44:27]:
What qualities do you think in that kind of dichotomy between a Holdco entrepreneur versus a single business entrepreneur? Like, what do you think are the differences in the mindsets or skills that you would consider important or crucial to running a portfolio of businesses versus a business?

 

Kelcey Lehrich [00:44:52]:
One thing that happens in a portfolio is you end up with portfolio effects. So much like in a venture portfolio or a real estate portfolio or even just a stock portfolio, the distribution of outcomes is not equal. You'll have outliers to the up and to the downside. So you have this constant capital allocation problem of your own time and attention and certainly financial capital of what are we doing this week, this quarter, this month, how am I handling this group of businesses that I have, which ones are growing, which ones are maintaining, which ones have challenges. And so you get this very different week or month or year of entrepreneurial operating when you're balancing kind of capital allocation as your primary challenge versus the focus company entrepreneur who's just going to grow their one thing. They've got this one boulder to push up a hill. I'm pushing six of them, but I'm running back and forth to whichever one is rolling backwards the fastest to try to get to stop, while some of them are just taking off like a rocket ship up the hill. It's just a very different dynamic of that portfolio versus that focus.

 

Jeffrey Stern [00:45:52]:
How do you think about, given the real kind of divergent, maybe goals of each company individually, the kind of overall incentive mechanisms that drive behavior at the portfolio level, that's an actor burnout. Profit sharing. I know those mechanisms matter a lot. There's a lot of divergent opinions on best ways to do them. Just how you've come to your own philosophy on what that looks like.

 

Kelcey Lehrich [00:46:22]:
We started with a very centralized, conglomerated profit sharing plan where everybody kind of got a share of the benefit. And as we've decentralized, we've also moved all of our incentives very decentralized to individual contributor scorecards and their own impact on their own business unit. And that's been a really good change for us. So I don't think we have it perfectly figured out at all. But trying to tie it as close to possible to the business objectives and to the levers that a contributor can pull to drive those objectives forward tends to be our North Star. So things like profitability, cash P and L metrics is where we try to.

 

Jeffrey Stern [00:46:58]:
Go to what are the accretive benefits to kind of very unrelated businesses as operating entities when you bring them together, is there anything surprising about that?

 

Kelcey Lehrich [00:47:14]:
Generally there is no synergy. Generally having a diversified portfolio is a good thing. It's kind of like Portfolio 101, right? Is something zig when other zags that's helpful. But other than lessons learned and maybe some institutional knowledge, there's very little from company A that really affects company B. And so again back to my like earlier comments of one day we might not do just consumer. If we owned a trucking company or a medical billing business or whatever, I think it would be the, the everything tastes like chicken layer of business. We have to have great people, we have to have a product or service customers want to buy. We need a delivery mechanism like it starts to get a little, a little bit.

 

Kelcey Lehrich [00:48:01]:
Everything tastes like chicken, right. And so I think for Justin and I being kind of high strung, harebrained, easily distracted entrepreneurs, a new challenge is always exciting. But getting our team members who maybe aren't us, right, they're by DNA, they're or team members, they're not founders. Getting them focused on something they can impact, something they value produces better results for the organization, for their careers, for the, for everybody.

 

Jeffrey Stern [00:48:28]:
Do you have like a North Star inspiration kind of proximate organization that, that you look up to? I mean the decentralized kind of conglomerate model, you know, Buffett or Munger kind of comes to mind. But is there an aspirational kind of organization that you.

 

Kelcey Lehrich [00:48:46]:
It's definitely not Berkshire Hathaway. I don't want to be the world's richest man and I'm not trying to do that. I really respect a lot of different holding company peers and friends. I've been to a number of events, both hold coconf and others where I've met people doing just the most fascinating things. I don't know that I have a good answer for your question of a particular organization we're trying to emulate. I think I want to just be the best version of what we're trying to be. What I enjoy though is meeting people doing it differently and comparing notes on the different ways we're all kind of doing similar things and seeing what nuggets we can glean from each other.

 

Jeffrey Stern [00:49:22]:
Yeah, I mean Sharon and the best of what other people have already figured out is kind of the fun of meeting other founders knowing that the aperture you might widen to do more than cpg. I am curious just your perspective on E commerce and where you feel it goes from here.

 

Kelcey Lehrich [00:49:48]:
Well we're recording this like two days before the China tariffs are real. So right now it's a total dumpster fire. Today's April 30th. When this drops, I don't know, we'll have lots of tariffs or no tariffs or it'll change probably. So right now it's highly uncertain and it's a really rough operating environment. So my answer is very jaded at the moment of like there is no guarantees right now, broadly speaking, aside from the current political climate and tariffs. I had been saying for a while and you probably find reference to me saying this in the last year or two that it's getting more competitive and the rent seeking big tech, Microsoft, Facebook, Google, Amazon, et cetera are going to continue to pull value out of the value chain and compete profits down if you don't have a really good value prop. And So e comm 10 years ago was very hacky.

 

Kelcey Lehrich [00:50:46]:
You could earn an outsized profit through arbitrage and hacks and a lot of that's really gone. And it's gotten to be more so of operating businesses that just happen to sell a product via an E commerce sales channel instead of E commerce marketers kind of hacking away at pockets of profit in the economy. So it's gotten more competitive, it's gotten more real business if you will, and a little less hacky.

 

Jeffrey Stern [00:51:16]:
On the opportunistic side of your business? What have been the most kind of interesting opportunistic opportunities that you've come across when you think about that intersection of luck and preparedness creating serendipitous opportunity like what in the opportunities you can't prepare for. I'm just curious like what what have been the things that you've been able to encounter coming at them from the mindset that we can be opportunistic that you've been able to do that otherwise, you know, affirm with a very structured, strict, you know, model would probably omit.

 

Kelcey Lehrich [00:51:52]:
For us it's been the distressed acquisition. So finding companies that have an immediate need for a transaction because of balance sheet impairment allows us to use the resources we have to move very, very quickly and get what is for us a very attractive transaction locked up.

 

Jeffrey Stern [00:52:12]:
That makes sense. What other earned wisdom do you feel is kind of most important that you've collected along the way that we haven't really touched on.

 

Kelcey Lehrich [00:52:23]:
Touched on most everything. We probably haven't gone deep on all of it. But without a hardcore E commerce or holding company audience, I don't know that you'll want to.

 

Jeffrey Stern [00:52:35]:
That's fair. That's fair. I could geek out on cohorts and retention and kind of all that. The T shirt versus subscription model kind of businesses. Do you. Well, do you. Do you. Typically within the.

 

Jeffrey Stern [00:52:51]:
The bucket of cpg, is there. Has there been an area of focus or is it. Is it really quite broad this year.

 

Kelcey Lehrich [00:52:59]:
Where you got everything from custom stuffed animals to jewelry to do it yourself, kombucha kits to pocket knives like it's am.

 

Jeffrey Stern [00:53:08]:
Yeah. Well, I'll ask then. What has building this business here in Northeast Ohio meant to you?

 

Kelcey Lehrich [00:53:19]:
Ooh, I don't think I've ever been asked that before. What do you think I was going to say?

 

Jeffrey Stern [00:53:26]:
I don't know.

 

Kelcey Lehrich [00:53:26]:
That's why I asked. I don't know if I have an answer for that one.

 

Jeffrey Stern [00:53:31]:
Beyond home, how do you think about it to the degree that it's relevant at all to the business or not?

 

Kelcey Lehrich [00:53:43]:
Ironically, Northeast Ohio has a great cost of living, so that's been a competitive advantage. It is not considered to be a hotbed of talent for E commerce or marketing. That's been a competitive challenge. We had to figure out how to build some of those capabilities and recruit some of those people and train them up, which has been rewarding. But there's probably many other easy places to build this business, including virtually and completely remotely would be probably a good start. And. Or places like Boulder or Austin or wherever. Los Angeles perhaps.

 

Kelcey Lehrich [00:54:20]:
But I think that this has been home for us for a while and it's kind of where we are. So we took advantage of the low cost structure and built everything else.

 

Jeffrey Stern [00:54:29]:
Yeah, cool. Well, anything else you feel that's left kind of unsaid that you think is.

 

Kelcey Lehrich [00:54:38]:
Particularly important, you covered a wide range. I can't think of anything off the top of my head.

 

Jeffrey Stern [00:54:46]:
All right, cool. Well, we'll close it out then with our traditional closing question, which dovetails interestingly to the one we just spoke about, but for a hidden gem in the area, completely unrelated, but something other folks should know about that maybe they don't.

 

Kelcey Lehrich [00:55:03]:
I feel like I grew up in Menor and I don't know. I didn't know we had a national park. I just. I don't know. My parents didn't take me there. I didn't realize it, but I think CVMP is great, particularly like the Kendall Ledges area. My kids love it. I like going there.

 

Kelcey Lehrich [00:55:17]:
Doesn't feel like you're in Northeast Ohio. Frankly, it feels like you're someplace more exotic. So I'm a big fan of what we have in the park.

 

Jeffrey Stern [00:55:25]:
Yeah, parks are beautiful. That's an awesome answer. Well Kelsey, I just want to thank you for taking the time sharing your story. It's really fascinating what you're building here and appreciate it very much.

 

Kelcey Lehrich [00:55:38]:
Thanks for having me.

 

Jeffrey Stern [00:55:40]:
If any folks had anything they wanted to learn more about or kind of follow up, where would you point them on?

 

Kelcey Lehrich [00:55:47]:
Online I'm easy to get ahold of. If you know the name of our website and how to spell my first name, you can probably email me. My social media is pretty easy to find as well. So if you Find me on LinkedIn or Twitter or drop me an email and mention this podcast, I'll be sure to reply.

 

Jeffrey Stern [00:56:03]:
Awesome. Well, thank you again.

 

Jeffrey Stern [00:56:07]:
That's all for this week. Thank you for listening. We'd love to hear your thoughts on today's show, so if you have any feedback, please send over an email to jeffreyoftheland FM or find us on Twitter oddleayoftheland or Sternfe J E F E.

 

Jeffrey Stern [00:56:23]:
If you or someone you know would.

 

Jeffrey Stern [00:56:25]:
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Jeffrey Stern [00:56:39]:
We love having on the show.

 

Jeffrey Stern [00:56:41]:
We'll be back here next week at the same time to map more of the land. The Lay of the Land podcast was developed in collaboration with the UpCompany LLC at the time of this recording. Unless otherwise indicated, we do not own equity or other financial interests in the company which appear on this show. All opinions expressed by podcast participants are solely their own and do not reflect the opinions of any entity which employs us. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Thank you for listening and we'll talk to you next week. It.