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Alexis Grant – Covering Company Exits at They Got Acquired

Alexis and I have gotten to know each other through our mutual interest in media and our two small but growing media companies.

Episode Description

My guest on this episode is Alexis Grant. Alexis and I have gotten to know each other through our mutual interest in media and our two small but growing media companies. We share thoughts, ideas, and advice back and forth all the time, and I’m excited to finally record one of our conversations.

Alexis founded a blog management company that was acquired by The Penny Hoarder, which then sold and gave her some starting capital for The Write Life, which she ran for a few years before selling that business too. Now she’s founded They Got Acquired, a media business covering small online business exits with a growing newsletter and data product.

We discuss all things teams, products, creating content, and one of my obsessions: the convergence of media and high-end products like data. Please enjoy this wonderful episode with Alexis Grant.

Clips From This Episode

Building Teams


Live Oak Bank — Live Oak Bank is a seasoned SMB lender providing SBA and conventional financing for search funds, independent sponsors, private equity firms, and individuals looking to acquire lower middle-market companies. Live Oak has closed billions of dollars in SBA financing and is actively looking to help more small company investors across the country. If you are in the process of acquiring a company or thinking about starting a search, contact Lisa Forrest or Heather Endresen directly to start a conversation or go to

Hood & Strong, LLP — Hood & Strong is a CPA firm with a long history of working with search funds and private equity firms on diligence, assurance, tax services, and more. Hood & Strong is highly skilled in working with search funds, providing quality of earnings and due diligence services during the search, along with assurance and tax services post-acquisition. They offer a unique way to approach acquisition diligence and manage costs effectively. To learn more about how Hood & Strong can help your search, acquisition, and beyond, please email one of their partners Jerry Zhou at [email protected]

Oberle Risk Strategies– Oberle is the leading specialty insurance brokerage catering to search funds and the broader ETA community, providing complimentary due diligence assessments of the target company’s commercial insurance and employee benefits programs. Over the past decade, August Felker and his team have engaged with hundreds of searchers to provide due diligence and ultimately place the most competitive insurance program at closing. Given August’s experience as a searcher himself, he and his team understand all that goes into buying a business and pride themselves on making the insurance portion of closing seamless and hassle-free.

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(3:46) – Alexis’ career journey

(8:52) – Why do you think ‘They Got Acquired’ would be a more interesting business to run?

(9:40) – What issues did you run into in previous roles?

(11:01) – What is They Got Acquired?

(14:16) – How have you approached building your team?

(16:18) – How do you determine what tasks you’ll work on vs. delegating to the team?

(18:40) – Do you try to focus on revenue-generating tasks over content or operations-related tasks?

(20:17) – What next task are you looking to delegate?

(23:41) – What role will you fill for your first full-time hire?

(24:28) – What would a full-time writer be able to accomplish that you can’t right now?

(26:04) – Is the research team for the database different than the writing team?

(27:14) – How do you ensure the media and date sides of the business interact with each other?

(30:04) – Are there any companies you find interesting that have a media arm alongside a high-end product?

(32:40) – Have you seen a media business buying a company that sells products best suited for its audience?

(36:05) – Have you thought about an event strategy at some point?

(37:05) – How do you think about competition in your space?

(41:52) – How do you balance what you want to do with your business vs. customer feedback?

(42:21) – What are you most excited about over the next 24 months?

(43:04) – What college course would you teach if it could be about anything?

(43:43) – What’s a strongly held belief you’ve changed your mind on?

(46:37) – What’s the best business you’ve ever seen?

Alex Bridgeman: It’s funny how many times we’ve talked, we’ve never actually discussed some of your earlier startups and jobs and work like the Penny Hoarder and some of the other businesses you’ve been a part of. Do you want to start there? Because I’m personally curious. I feel like we haven’t- I feel bad we haven’t talked about it before because I’ve it’s really interesting and we haven’t dived into it. I’d love to start there.

Alexis Grant: I started my career in journalism. And I worked at US News and the Houston Chronicle for a few years, which I really loved. Like I loved being a reporter, and I thought I would never ever give it up. It’s like an excuse to go to all the interesting events and stick your nose where it might not otherwise belong and ask questions. And I just loved it. It was fun. And then I left my Houston Chronicle job to travel for a while. I went backpacking on my own through West Africa and Madagascar, a bunch of French speaking Africa. And then when I came home, I was looking for a job. And I wanted to end up back in DC, where I had spent a couple of years previously, and ended up getting a job at US News and World Report. But I only stayed there for a year. I was covering careers. So, I’d have to cover the jobs report which is really fun and learn about that. But what I realized during that time is that I had a lot of opportunities for what had become my side business. So, when I came back from traveling, I was living with my parents for a while. And when I was looking for a job, I started taking on clients for social media and online work. And I had to put that to the side when I took the job at US News. And pretty soon into my work at US News, I started to realize I was getting more inquiries on clients, and I was working a lot. I didn’t have a family, I didn’t have a partner at that time. So, I was working my regular job, then on the weekends, I was doing everything else. And I ended up deciding to leave that job and pursue the business full time. So that was the first time I really got into running my own business full time. This was in like 2010. And I was also experimenting with eBooks at that time, which kind of ties into my career now and just started realizing that, wow, I could create something without permission from anybody else, put it on the internet, and people would buy it. And I just thought that was so cool, especially as a writer. I got to write and sell whatever I wanted. So, I eventually morphed what started out as a freelance business into a small content agency. And our specialty was running blogs for businesses. So, this was from 2010 to 2015 when content marketing was sort of starting to get big, and a lot of people wanted to have content to grow their sites, but they didn’t know how to do it. So, we would do it for them. So that was the business that became my first sale. It was purchased by a company called the Penny Hoarder. And that’s a personal finance media company. They bought us in an acqui-hire. So, what happened was myself and several members of my team, we went in house there to grow out the content operation there. So, I was a second employee there. And the founder was already like on a roll; he’d done a great job with the company. And he had actually, a year and a half before he bought my company, we started working together because he was one of our clients at the agency. So, when he bought my company, we had already been creating the content for the Penny Hoarder for a while and knew that we worked together really well. So, I stayed there for a bunch of years and helped grow out the content operation there. And I left in 2019. And I picked up a side project called The Write Life, which is something I had launched years before when I was running the agency kind of as a fun passion project, but also as a way to apply the systems that we were using for our clients to our own asset. So, I noticed early on, like oh, we’re doing all this work to grow the audiences of these other companies’ blogs, and if they leave us, we only got paid for that month that they paid us for. Like what if we had our own asset where we apply these same systems and strategies and then we get to keep that asset over time. So, we launched it in 2013, I think it was, and I ended up selling that in 2021. So, when I left the Penny Hoarder, I took a year to kind of play around with it. I was figuring out if I wanted to run this site full time again, if I wanted to get back into it. Because while I was at the Penny Hoarder, I really didn’t spend much time on it. It was very much a side project because I was busy with the job and life. What I realized was it felt like- I wanted a new project. It felt like something I had done in a previous life. And it wasn’t exciting to me anymore. So, I ended up selling that website, which kind of cleared my plate so I could start They Got Acquired.

Alex Bridgeman: Did you sell it on MicroAcquire, I think, right?

Alexis Grant: No, I sold it directly. I had a bunch of people who had asked me over the years if they could buy it. So, I sort of had a pool of people who I knew were interested. But I actually ended up selling it to someone who wasn’t even in that pool. Just through word of mouth, when I decided to sell, I had a few people who were interested in it. I ran a bidding process. So, I didn’t need like a marketplace or broker or anything.

Alex Bridgeman: Gotcha. And so why do you think They Got Acquired was a more interesting business for you to run than that business you just sold?

Alexis Grant: The first reason is the topic. I mean, The Write Life was about how to make money, how to make a living as a writer. And I just I started my career as a writer, and I still am a writer at heart, but I really am much more on the business side now. And I just felt like freelance writing was who I was a decade earlier. So, in terms of the topic, when you think about M&A and just how do you sell a small business, to me, I had a lot more to learn there. And that made it more interesting to me. I kind of knew the pain points because I’ve been through two small acquisitions myself. So, I knew what the problems were for people in that position, and I felt like it could address that pain point.

Alex Bridgeman: Yeah, what problems did you run into at both the Penny Hoarder and Write Life?

Alexis Grant: I mean, I didn’t know what I was doing, so that was the biggest one. And I didn’t know how to find someone to help me. And I think as a business owner, a lot of us, we have our heads down running the business and we’re figuring out how to grow that business. And then when it comes time to sell it, it’s a totally new thing to learn. It kind of reminds me of when you get married. You hopefully only go through that once, and you have to figure out who all the vendors are and what all the venues are and all those things, and you just use that information once and then you move on with your life. I felt like there was a big learning curve for figuring out how to sell a business. And I didn’t really know where to go for information about how to do it. And the second piece, which is something we’re also directly applying at They Got Acquired is, I mean, I literally was trying to find comps by hand across the internet by reading articles and stuff to figure out how much should these companies be worth. And I wish there was a place where I could have just said, hey, I want to look at businesses that are in this industry of this size and how much they sold for. And so that’s one thing that we’re doing at They Got Acquired.

Alex Bridgeman: Yeah, that’s a really interesting piece that we talk about a lot is the data side of They Got Acquired. We were just talking about GF Data getting acquired too and how interesting of a business that is and in a very similar way as They Got Acquired. So, what is They Got Acquired? Can you kind of break down the business, what it does, and then let’s dive into the data piece.

Alexis Grant: Yeah, so we’re a media company on the front end, but I’m hoping that years from now, I’ll be able to say it’s a data company instead. We tell the stories of founders who have sold their businesses and how they did it. And on the back end, we’re collecting data about all these acquisitions. So, we’re covering small market M&A, and the deal size has to be between 100,000 and 50 million. But most of the deals we are covering are six or seven, maybe low eight figures. And, yes, so our goal is to really help entrepreneurs sell their company. And some of those folks, I think it’s mostly useful to first time sellers who really don’t know where to find the help that they need or have to figure out what they’re doing to maximize the value of their business. But my hope is that it will also be really helpful for people who are going through sale the second, third, or fourth time if they want to get data around acquisitions that might look like theirs, and also helpful for people like brokers and lawyers and any support professionals who work in space.

Alex Bridgeman: Yeah, it’s funny thinking about the different audiences you could have that aren’t the specific target one that you have in mind. Like there’s all these peripheral folks who are interested in that information, but maybe from the get-go you wouldn’t have thought would be interested in that stuff until you start seeing them pop up in your newsletter. What have been some of the most interesting different groups of folks who have taken an interest in this type of data?

Alexis Grant: Yeah, I mean, I actually think that the support professionals might end up being a big part of our target demographic over time. Because if you think of a founder, you only sell a business once, or maybe you sell a few businesses, if you’re lucky, in your lifetime. But someone who works in the space and is helping entrepreneurs either buy or sell, they go through lots of transactions. And so, they might need access to our data more regularly even than a founder would. So even though the idea originated around helping founders, I think, actually, it might be more useful and a better way for us to monetize long term to make sure that we’re also meeting the needs of other people.

Alex Bridgeman: Yeah, certainly. There’s the two folks I was mentioning who were customers of GF Data, and I assume, I think they still are, they invest in small businesses. So there’s probably a lot of folks who maybe aren’t business owners but own multiple businesses or are search fund investors, like we have a lot of search fund investors on this podcast, who’d probably be interested in that kind of data for the primary- maybe not for the exit acquisition because you’re hoping to sell for a much larger amount and maybe like 80 to 100 million, but for that initial buy of any enterprise value between like $5 and $30, $40 million, that’s got to be really interesting data. There’s a whole bunch of different audiences you could think of for this type of information.

Alexis Grant: Yeah. And I think I have more to learn about what the needs of those different groups are. And so, what my goal is here is we’re starting by meeting the needs of entrepreneurs. And I’m really curious to see as we start to put some paid products out who buys them. And I’m hoping that’ll give us some more hints about which directions to go in in the future.

Alex Bridgeman: Yeah, that’d be awesome. And this is all bootstrapped. You’ve bootstrapped this business and you have a team of freelancers. I don’t believe you have any full-time employees yet. Can you talk about the team makeup, and kind of how you’ve broken up each role amongst your team and what that looks like for you on a daily basis too?

Alexis Grant: Yeah, yeah, sure. So, I am bootstrapping, which has been more of an adjustment than I thought it would be because I’ve only worked for bootstrap brands. But the last one, when I was at the Penny Hoarder, which is fast growth, it was a bootstrap brand, but it had a lot of resources. So, I had a team of like 60 content creators and plenty of resources. And it’s so different now starting from zero and being bootstrapped. And I’m putting some of the money from my previous sale into this company, so that’s helpful, because we’re not yet paying for our expenses. We will be hopefully soon, but we’re not there yet. So, it’s an investment on my part. So yeah, we have a team of about 10 freelancers. And right now, what that looks like is we have an Operations Coordinator who does a little bit of everything, and just helping us make sure things move smoothly. Most of those folks are content creators. So, we have a Podcast Producer, who helped us with the first season of the podcast, which we just completed. And we did a narrative style podcast, which requires a lot more energy and time and effort than a pure Q&A. So that’s a bigger position than it might sound like if you think about someone who’s just editing a Q&A. And then we have a bunch of reporters and an editor and a designer. So, I’m hoping that eventually we can hire some other part time folks to help on things like growth, marketing, maybe more on the business side. But at the moment, I’m having to be really thoughtful about who I bring on and what pieces I keep for myself versus what I hire people to do.

Alex Bridgeman: Yeah, that’s the kind of next question I had or was off the top my head was how do you determine what you’re going to work on? Especially considering we’ve talked at length about not being able to work a full 40 hours or like a founder might work 60 or 70 or 80 hours on their business. You can’t do that, so you have to be very selective about what tasks you work on versus what you hand off to other folks. How do you make those decisions on what you work versus others?

Alexis Grant: That’s been my biggest challenge for sure this time around. Because when I was younger, and I used to start businesses, I just worked all the time because it was fun, I really enjoyed it. So, I just wanted to be working on it. And now I have a family. And I also don’t want my entire life to be around work. So, I’ve been tracking my time. I’m working between 25 and 30 hours a week, which is probably where I’d like to be, but also doesn’t feel like enough at this early stage in the business when there’s so much to set up. So, I’m definitely still doing some things that I would like to hand off. But I need to get our revenue up before I can do that more. So, for example, you asked how do I think about what I keep, I mean, one easy thing that I don’t really ever do is writing. It’s not easy to do. But it’s easy for me to delegate because there are a lot of people who can do that. And it’s hard to find the right people. And I do spend a lot of time trying to find the right reporters and writers for the job. But once I have good people on board, they can do the writing. And that frees up a lot of time, if as a founder of a content company, you’re not doing any of the writing, I do do some of the editing. I probably do 60 or 70% of the editing right now. I have an editor who works some hours for us each month. I’d like to- that’s a piece that I would like to- it’s the next in my brain, it’s the easiest to hand off to have someone else do the editing, but I just need to have the funds to do it. So that’s like the hardest part I think about going from a well-resourced company to starting from zero and your bootstrapping is I can see the path forward. But I am having to make compromises about what gets done when. And I feel like when you’re at a VC backed startup or a well-resourced startup, you can move forward on everything at once. And I don’t feel like I can do that right now. It’s like I can move one train forward, but then the other one doesn’t move until I get over to it, or I have someone focus on it. So, it feels like it’s never moving quite as fast as I would like, even though I hope from the outside it looks like it’s moving.

Alex Bridgeman: Do you have a focus on within just the tasks that you handle yourself? Do you try to focus on revenue generating tasks over operations content related tasks?

Alexis Grant: I think eventually I will be able to, but in the early days, I’m still figuring out what everything is. So, if you think about starting a content brand from scratch, and this was like a really rude awakening for me to start something new again and be like, oh, yeah, I have to figure out what does the content even look like? What’s in it? How long is it? What do we include? What’s important? And being really in the weeds on that so that I can give guidance to people who come on board to help with it. So, I’ve been in the weeds while we’re creating the first iterations of a lot of things so that I can help to set our own style.

Alex Bridgeman: Is there some thinking in your head about or some equation or something you’re running or you’re trying to balance the revenue generating tasks that you work on versus stuff that’s not making any money and just is like running the business?

Alexis Grant: Yeah, I think of it more as what can only I do? And admittedly right now, I’m still doing things that I could delegate, but I try to weigh it towards, what could only I do? And to me, those things are finding the right people, sales for advertising. I mean, eventually, I could give that to someone else. But to be honest, that hasn’t been a hard piece for us. So, I’m just keeping it under me for now. What else? Really just like the guidance, guiding the content strategy. So yeah, I think about what do I feel like needs my touch right now with the hope of being able to delegate more as we grow.

Alex Bridgeman: What do you think is that next thing that you can delegate? Is it editing? It sounds like it was editing for a little bit.

Alexis Grant: Yeah, that would be an easy one. Although it’s hard to find. It’s hard to find editors with the expertise that we want. And I need to train that person and feel really good about handing everything to them. But to me, that’s- the reason why it feels like an obvious one is because it takes up so much time. It takes up time, and it takes up brain space. And I find it challenging to go between thinking about high level, how do I move the business forward and how are we making money and how is that going. And then when I’d have to switch gears and work on editing, it’s very nitpicky. Quite frankly, I don’t feel like I’m as good at it as I was years ago because I’m not- it’s not my main thing. The editor I work with is way better than I am. She’s does that all day every day, and she catches everything. But I find it hard to context switch between those two things. Like one is like more big picture, putting the pieces in place so everyone can do their jobs, making sure the business runs smoothly. And then to switch over to editing and just thinking about the details of did this person start the story the way we want it started? Are all the details in here that we want? Fact checking, like did they pull that quote correctly, if I’m working with someone new who I just hired, like all that little detail-y stuff, I try to do that. I get up early a lot of days, so I can get like an hour of work in before the rest of my family gets up. And I try to do the editing in that hour because I’m much better in the morning, and I find can focus. Because it’s really hard for me after I look at my to-do list of all the business things to then spend 45 minutes editing a piece.

Alex Bridgeman: Yeah, certainly. I feel like running a business is just death by context switching. And your goal over time is to do less switching, and eventually having other people do that switching for you or just only focusing on that.

Alexis Grant: Yeah, definitely. But editing is also, it is one of my core competencies, like I’m pretty good at it, and it’s in my background. And it makes a big difference for the business. And it’s expensive to hire a good editor. So, from that perspective, I feel like that’s why I have chosen to outsource some of the other things and keep that until I can afford it.

Alex Bridgeman: Yeah, editors are expensive. The editor we use is on the same like expensive range, but he’s awesome. And he has a full-time role with the Wall Street Journal, so he can’t spend full time with us. But the 20 hours or 10 hours or 5 hours we get with him on a weekly basis is worth its weight in gold. I’ve found that you get what you pay for with a lot of good freelancers who have done this for a long time and are much better. For example, with the illustrating, taking our content from a Word document file to a finished PDF that we can send to a printer. I initially tried to do it myself, and then quickly realized that there are people who are very, very good at this, who could do it much, much faster, and much, much better. And it’s better just to go pay them and let them take their expertise and help you.

Alexis Grant: Yeah, I am missing having full time employees. I don’t aspire to grow a huge business that has- I want to grow a big business revenue wise and impact wise, but not employee with what employees. But I would like to have a couple of full-time employees. So, I’m hoping that we can get there in the next couple years.

Alex Bridgeman: Who do you think your first full time hire is going to be?

Alexis Grant: A writer, and I already know who she is. But I got to get to a point where I could bring her on. I’d love to hire some of the writers that I’ve already trained for other ventures, just because I know that we work well together, we won’t waste any time in terms of getting started, it will be a good fit. And there’s just so much that I could- it would be easier for me to manage a writer full time. So, I still would want to have other freelance reporters because I believe it’s important to have a diversity of perspective in reporting. So, we want to have different bylines on the site. So, I wouldn’t get rid of that. But there’s a lot of other things that need to be written. And there’s even I think some light editing that a writer could help with if they could come in.

Alex Bridgeman: So, what additional products or content would a full time writer be able to help you more with or help you start that you’re not able to do today?

Alexis Grant: Well, just writing more pieces for the website. Right now, we’re publishing three posts a week. And usually, two of them are stories about entrepreneurs who have sold a business and one of them is what I call like a resource post. So, it just explains something that has to do with the process of selling. So we have a post about mistakes you don’t want to make in your LOI, in your letter of intent. Or even like, what is EBITDA, explaining that for people, so they understand how that fits into selling your business. And then even, so we’ve just gone through- we just tried some paid advertising where we put ads in other newsletters and writing the copy for that. And we’re starting to come out with our first reports that are going to be paid products that people can buy, and we need to write the landing pages for that. And then we also do newsletters twice a week. And that has to be written too. So, there’s just a lot of writing related tasks. There’s even some- I’d love for us to repurpose more of the content that we’ve already created. We have some really solid content already. But we could do, for example, I have an idea in our queue that’s do a post that rounds up the acquisitions on companies that have to do with podcasts. And that’s an easy one. We’ve already done all the research. And we have stories on different companies on the site, but just bring it all into one post. So that can be a new post. Stuff like that, just taking stuff we’ve already done and making it go a lot farther.

Alex Bridgeman: Is the team that’s doing all the research for the database, is that a separate team than the writing team for the newsletter?

Alexis Grant: So, I have one researcher who doesn’t have a background in journalism or writing. But her strength is curation and online research. So, she’s doing a lot of the initial research to get each company into our database. But then beyond that, we’ve reached out to each team, or each company or the founder and try to get information about the deal. Because they’re pretty much all private deals. There might be- I mean, there almost always is information on the internet that we can find about it, either another outlet wrote about it, or there’s a press release, or they wrote about it on a blog, or there’s a podcast interview. Like you can piece together all these different sources of information. But there’s no like FOIA request you can make to get the information or database, like no one else has collected this information. It doesn’t exist in someone else’s database. So, you have to go directly to the source and ask them for the data themselves. So, we have a reporter who writes each of those stories, and through those stories, they end up collecting more data that the researcher didn’t find that we can then add into the database. So, it’s very manual.

Alex Bridgeman: Another common topic of discussion for us is the combination of the two sides of the business with media and your data product. So how do you make sure that the two interact? You talked about it just a little bit there, but how do the two- how do you make sure that the two are interacting with each other, and the media side is marketing the data product, and data is going to media and that information is being exchanged back and forth?

Alexis Grant: Well, we’re going to do a free product first, which is kind of like a sampling of what we collect. And it’s 21 companies that have sold in 2021 for six or seven figures. And they’re across industries. So just to give you an idea. And what you get with that is it’s a PDF, basically a slide deck that has the stories behind all the acquisitions, and how they found their buyer, all the metrics we have, and then you also get a spreadsheet along with it with all the numbers in it. And so, this all comes from our database. We’re basically using the database we put together and pulling out of that database to create the products. So, it’s a direct correlation. Like anything, the database is the source of truth for us, but we’re using that to create other things. But my goal is long term, I would like to have a way for our audience to access the database themselves. Like they can sign in, they use a log in through a subscription perhaps, and be able to pull whatever data they want. But it’s going to take us a while for us to build it. So, while we’re building it, we’re pulling out slices. The second slice we’re going to do is content companies. So, we have one that’s almost ready that’s going to be about 20 content companies that have sold in the last few years for six, seven, or eight figures. And so, our goal is to get some of these out and see how people respond to them. Because even though I think we’ve found, I would say, in terms of- our content is resonating with people. I feel like we found product market fit for content, if that’s the thing, but we haven’t- we’re just now starting to try these paid products. And I don’t know yet if people are going to buy them. I hope they will. And if they don’t, I feel confident there are other ways to monetize this business. We’re also doing sponsorships, for example. But we’re still in the early stages of experimenting and seeing if it’s going to work.

Alex Bridgeman: And you’re building the database in Airtable, right?

Alexis Grant: Yes.

Alex Bridgeman: And so, when you think of the user interface over time where folks can log in, is there some plugin with Airtable that you’re able to get?

Alexis Grant: There is actually. Because I originally, when I first started this, I was thinking being able to directly access the database would be a long ways off because we’d have to build the UX and it would have to look pretty. But no, there’s no code tool, so you can just plop right in the top of your Airtable and let people look through your Airtable database on their own. So, I actually think that part will be way simpler than I originally envisioned. But it still will take us a while to collect all the information.

Alex Bridgeman: One of the most interesting things that I’ve observed with media businesses that you have too and we’ve talked about before is when media businesses have, they monetize the content itself in some way through ads or paid subscriptions or both or something else. But then they also have this other product down the funnel that they’re selling, whether it’s software, data, real estate, something else. FLYING Magazine with real estate is kind of a fun example I’ve enjoyed studying. Can you share a few examples of companies that are selling some other product that you find really interesting as a business model, and some of the advantages of having a media business if you already sell that high dollar value product?

Alexis Grant: Yeah, I think the reason this is interesting to me is because having come from the content side, it’s always easier for you to think about the content first. Like I know the content has to be high quality, so people actually want it. But then how do you make money off of that? And I think a lot of content creators that don’t think about that in the beginning end up in this conundrum of how do I make money from my content? And like you said, one way to do that is by selling direct access to the content. So, maybe it’s a subscription or something. Or you could layer on a- I mean, I think it’s cool, one of my kind of long term dreams, I don’t know if I’ll ever do this, but to layer on a SaaS onto a content company because it’s really simple, and it’s something that you can get paid for again and again over time. I mean, we’re sort of going to do this at They Got Acquired because our plan is to let people access the database through some sort of subscription. But what’s cool about that is it’s not a product that’s totally separate from the content creation process. Like, we’re reporting and we’re creating media. And at the same time, that same media can be used in the database for the paid product. And so, it’s almost like killing two birds with one stone. You get a lot more value out of it. So that was one thing I thought about when we were first starting is how can I build a media business in a smarter way than I’ve done it before. And to me, that’s a built in, I mean, if it works, I think it will, a built in way to monetize. But the Hustle is another great example that people understand because a lot of people know about it, whereby the Hustle sold the HubSpot because HubSpot wanted them because they had a product they wanted people to buy. And the Hustle is the audience; they bring the people that might actually buy it. So, it’s just cool to see media companies become a really strategic move for product companies because they know that if they bring that audience in, they can turn a lot of value out of that audience.

Alex Bridgeman: You talked about media companies also are often being a strategic acquisition by someone who could use that audience to sell their product. Have you seen it happen the other way where the media business hears about some product that their audience is using all the time and decides to go buy that company that makes that product?

Alexis Grant: I’m sure I have. I don’t know if I can think of an example. I keep trying to convince my husband to do this, actually, because my husband, his name is Ben Collins, he runs a site and a training course about Google Sheets. And he has a big audience. I think his newsletter list is about maybe 40 or 50,000 people. And they’re all really loyal. And they’re there for his- he teaches them how to use Google Sheets. And I keep saying to him, either build or just go buy somebody else’s extension or something. He could probably buy an extension. This is like thinking really on the micro level. But if he bought an extension for $10,000 and turned around and sold it to his list even once, never mind like a subscription fee over time, he could easily make a profit on it. So, I think that’s a really interesting way. What I love about it is it’s simple. Like it’s so easy to go after these huge businesses that are going to change the world. But I think the models that are simple, those are the ones that really interest me.

Alex Bridgeman: Yeah, that is so interesting. Because even if the business, like your husband’s example of going after a plugin or extension of some kind, that plugin on its own might not be worth that much if someone’s just trying to buy just the plugin. But if you have that audience that you know that you can automatically plug it into a much larger group that you can market to, suddenly that product is much more valuable to you. But you can still buy it for the face value of that business, which is much, much smaller.

Alexis Grant: Yeah, well, a lot of the makers have the opposite problem from the content creators. It’s like they know how to make a product that’s valuable. They don’t know how to get people to go to it and buy it. And likewise, a lot of content creators know how to create great content and build an audience, but they don’t know how to create something that people are going to pay for because sometimes people won’t pay for content. So, I think, yeah, it’s really interesting to think about how can you combine those two things and whether it’s at like a big macro level, or it’s just two small companies that are merging, I think it’s really, that potential there is really interesting. I would love to do that myself sometime, and maybe at They Got Acquired some time we will figure out there’ll be some really specific tool that people want to use that we could layer on top.

Alex Bridgeman: Yeah, there’s going to be tools or even like a business brokerage that does online businesses primarily you could probably go buy. MicroAcquire is probably too big at this point. But there’s probably other tools and things that people use in acquisitions that you could go acquire and use your audience to help market that. There has to be a broader investment strategy like that that you could go execute one day.

Alexis Grant: For sure. I mean, well, I think the broader investment strategy too, beyond that, and a lot of companies do this, is a lot of content, the smart content companies, is you partner with a much smaller company that offers something like this. And even if there’s an affiliate relationship, you earn when you send people to them over time, but you also maybe take a bit of equity in the company, because that means that not only are you- you’re helping them grow, and you’re making money as they grow, and they’re making money. So, it’s a win-win. But then you also get a piece of that over time. So it’s a way to magnify your power as a media company, which I think is really cool.

Alex Bridgeman: Have you thought about an event strategy at some point? Is that in your future? Or do you just think that that’s too far out in the future and data and the newsletter is going to be, for the next couple years, the more upfront focus for you?

Alexis Grant: I would love to do an event, but it’s mostly from a selfish perspective. Like I could see bringing a small group of passionate business owners to where I live in West Virginia and hiking during the day and then having some conversations about what we’re building because that just brings me energy. But I haven’t really thought much about how an event strategy would improve the company’s bottom line or anything. I think we need a community at some point. But it’s just like there’s so many things that we could bite off. And we’ve really got to stay focused. And also, I feel like as the year goes on, I don’t even like planning out too far ahead because things change. And we might see an opportunity that feels better than what’s even on our roadmap. So, I’d like to really stay open to that.

Alex Bridgeman: How do you think about competition for other media businesses? I can’t think of any others that are very close to They Got Acquired in terms of what they do or focus on. But in the media sense for the media industry, like how do you view competition? Do you welcome it because it means that there might be more advertisers interested in that space? Or does it make me nervous because then maybe they start to encroach on your territory? Like, how do you think about competition?

Alexis Grant: I don’t care about competition because I know I can be better. And that might sound crazy. But I think a lot of people who want to be growing the biggest business on the planet, they want to snuff out all their competition because they want to be the one. I don’t want to be the one. I don’t want to build the billion dollar business. I want to build a business that’s big enough and get to serve a lot of people and serve my family and serve my team. But I believe that I can do that while existing alongside a lot of other people. And so, I look at competitors as collaborators – how can we work together and lift each other up. And even at the stage we’re at now where it’s still early, there’s still ways to help even competitors that are bigger than us. And quite frankly, it’s been really interesting. I’ve learned a lot about this space since starting the site. And there really aren’t, in the media piece of it, there really aren’t that many straight up competitors. I mean, I think every company says this, we don’t really directly compete with anybody, we are different than everybody. But there just aren’t that many content sites dedicated to what we’re covering, which is, I think, why it’s been relatively easy to find advertisers because they’re desperate to reach these people. And if you look at the information on the internet about how to sell a business, almost all of it comes from someone who has a stake in whether you do it or not. So, they’re from brokerages, M&A advisors, financial advisors, and not to say any of its bad, it might be great advice, but a lot of it is written in a really stuffy or boring way that’s not accessible to readers. And until now, there really just wasn’t or I haven’t found another site that covers this topic in an accessible voice that is truly like an independent voice that’s saying like, here are your options, and here’s how to do it. And if you choose, we’re not going to not make money if you don’t choose us, kind of thing. So I think there’s just a lot of- and it’s also a very niche market. So that’s another thing to think about. And I’d say it’s more niche really than anything that I’ve ever- any market I’ve ever gone after. But I also think there’s potential to broaden it. So, in some way or another, you could really serve all owners of online businesses because even if they don’t want to sell immediately or in the next five years, a lot of the things that we’re talking about are best practices for building a good business whether or not you want to sell.

Alex Bridgeman: Yeah, that’s a good point. Is some of that thinking or perspective on competition not being that important, is some of that influenced by your time at the Penny Hoarder? Because I imagine there’s a lot of competing media sites and blogs that talk about saving money or investing and growing your personal wealth or buying a house, that sort of stuff. How much perspective did you gain from the Penny Hoarder in terms of competition?

Alexis Grant: Actually, the founder of the Penny Hoarder, who’s a great guy, Kyle Taylor, he actually has a very different perspective on competition than I do. So, we didn’t really take that approach at all at Penny Hoarder. I mean, but his ambition, and he’s achieving that, is to be the best, biggest personal finance media brand. So, it’s a different approach than, I think, what I’m taking. But I think he would- we did agree on a lot of the finer points where like, don’t waste too much of your breath on competition, for example. I think where my perspective on competition comes from also is necessity. Like I have 25 hours a week to work. I do have a list; I have a spreadsheet of other companies that produce data that’s kind of like ours, so I can try to go through them and learn from them. But to be honest, I haven’t even done that that much; I probably should. But it’s really a matter of if I want to move this brand forward, what’s the most important thing I have to do right now. I can’t do everything. I can’t be on top of everything. So, I have to pick and choose what gets my time. And I feel like even if there’s other people out there doing something similar, and yes, I may get ideas from them, but I also just want to go out and do it better anyways. And so, part of me thinks, and maybe this is a naive way of thinking, I should just go out and do what I want to do and not even look at what anyone else has done. Because it might influence the way I think about it. And I think over time, that’s good. But maybe in these early stages, I’d rather have- I have a clear vision of what I want to do. And I don’t want what a competitor is doing to muddy that.

Alex Bridgeman: Yeah, how do you take a balanced view of what you want to do with your business versus what feedback you get from customers or vendors of yours or your team? Like, how do you balance the two?

Alexis Grant: They mostly feel aligned at this point. I mean, what people are asking, if someone asks for something, I want to do it because I want to provide what they need. So, we’re still really- we value that feedback right now. And so far, it hasn’t felt like they’re not aligned.

Alex Bridgeman: What are you most excited for in the next 24 months or so?

Alexis Grant: 24 months seems so far off to me. In startup world, it’s like, who knows where we’ll be by then. Right now, I’m just focused on getting to this next phase where we know that people are going to buy our paid product. And then I’m most excited about growing the brand because I think there’s a lot more we could do around audience growth that we haven’t done yet. And I think once we put that time into that piece, it will explode the brand. And hopefully, we’ll have all the foundational pieces ready so that it can take that.

Alex Bridgeman: That’s going to be awesome. We could chat all day, but I want to make sure we get out on time and get closing questions. If you could teach any college class you wanted, what would you teach?

Alexis Grant: I don’t know a fun way of saying this, but I would teach something on like clear communication, or saying what you need in a way that someone else is going to give it to you. Because I feel like so many- and by saying, I more mean writing because I’m much better at writing than talking. But I feel like being able to write in a way that is effective basically, even just through emails, is really helpful for a career and a life generally.

Alex Bridgeman: There’s a lot of things that need a convincing word or two for sure. What’s a strongly held belief you’ve changed your mind on?

Alexis Grant: I had to think really hard about this because, and it made me realize I don’t change my mind that often, which probably is not a good thing. But I definitely thought when I was younger, that I could outwork. Like I can work to solve any problem; working harder would solve any problem. And I don’t believe that anymore. I think I just see now that people in life have different circumstances that make it hard to do that. And working harder is not always the option. It’s one way to go. But it’s not always effective and it’s not always possible. And I think I just had to figure that out with life experience.

Alex Bridgeman: Yeah, how does that carry over to your business too? Because you have to be very selective. Of course, we talked about this, about what you want to work on, but it really forces you to work much more smartly than you could if you had full availability, for sure.

Alexis Grant: Yeah, I mean, I don’t think parents generally waste much time at work. That’s why they’re some of the most effective or efficient people that you’ll meet. When you run your own business, there’s no such thing as busy work. It’s like you only do the things that are actually going to move the needle because otherwise you don’t get paid. But yeah, I feel like having fewer hours to work has helped me. And that’s my choice, by the way, too. I want to spend that time with my family and doing other things. So, choosing to work less does force me to pick the priorities better. And I feel like I’m always working on that. It’s always a work in progress. But for example, we’re going away, we’re about to go away for a month to see my husband’s family overseas. And I really- this is really stretching me right now. Because I do not feel comfortable about leaving the business for a month this early on. And I’m all about taking long vacations. It’s great. I’ve done it many times before. But I feel like we’re so early, and we’re still putting systems in place. And I don’t have enough of the right people trained to just peace out for a month. But we’re doing it. And in some ways, it’s really good because it’s a forcing function. And actually, I’ve heard women say this about having a baby, like going on maternity leave, it forces you, like you have a deadline, you have to have things delegated and in place before then. And I feel like this trip is helping me speed up that process. So, it does still stress me out, but whenever I get stressed out, I’m trying to think about, okay, what’s the silver lining here? This is forcing me to really hone in on what’s important, what has to be done when I’m gone and make sure that it gets done either by me ahead of time or by someone who I’ve taught to do it.

Alex Bridgeman: Yeah, that’s something I think I’d love to get better at too is forcing myself to work on stuff that isn’t busy and ignoring busy work. That’s one I could work on. What’s the best business you’ve ever seen?

Alexis Grant: I don’t know if I can think of one specific business. But what my brain goes to is the simple businesses that we were talking about earlier. Those are the ones that are really interesting. I can give you an example. This is a startup and they’re still in early stages. But I was talking to this woman the other day, and she was demoing it for me. It’s for editorial teams who need help with style. And if you have a question of what’s the style, you can just- it’s a Slack chat bot, basically, where you can ask them what the style is, and they’ll respond. So rather than having to like go into AP style book and look it up, or sometimes at your company, usually you’ll have some things that are a different style than AP Stylebook anyways, and rather having to search through your company’s style book, you just ask the bot what is the style. And when she explained this to me, I thought- like she didn’t have to convince me at all. We don’t use Slack. If we did, I would use that in a second. I was like, this is brilliant, you don’t have to explain. And I think I’m curious to see what she does with the business and how they’re able to grow it. And I don’t know how successful they’ve been. But the idea, she could explain something to me or show me something, and the light bulb went off. And I went, that is so simple and so solves a problem of mine, like I would pay for that in a heartbeat. Those are the things that I get excited by.

Alex Bridgeman: That’s really cool-

Alexis Grant: I think it is called Stylebot. But so I should say what it’s called before if I’m going to talk them up. I think it’s called

Alex Bridgeman: That’s cool. So is there some back end database with all these different styles and formats and it just searches through based on the words you typed in?

Alexis Grant: Yeah, you get to customize or they help you customize it based on your company’s style.

Alex Bridgeman: Is it totally automated at this point? Or if it’s too hard, will someone come in and start replying for the bot?

Alexis Grant: Oh, no, I think it’s automated. I think that the back end, they’re still- my understanding was they’re still early enough that there’s a lot of manual work done on the back end and to get you set up and stuff. But it’s a bot that responds every time you ask.

Alex Bridgeman: That’s incredibly cool. That is so cool.

Alexis Grant: And it’s so fast. Like what a brilliant idea.

Alex Bridgeman: Yeah, no kidding, especially since it’s all automated, instant. It’s better than Google. Yeah, that’s interesting. It’s one of the first businesses I’ve heard of that could replace Google for something like that, where it’s accurate, really fast, and it’s all focused on that specific topic. Of course, it’s not going to replace Google for everything else. But for that specific-

Alexis Grant: Google can’t tell you your own style, though. Like if you have, for example, at our company, AP style writes out 50 percent, they write out ‘percent’. We do 50% with a percentage sign, which a lot of financial media companies do that because it’s arguably easier to digest. Google couldn’t tell you that, what your style is. So you almost have to have it somewhere, it’s like in your internal docs. So this is like an extension of that internal document, I guess.

Alex Bridgeman: That’s so cool. That’s fascinating. Thank you so much for coming on and sharing a little bit about your business and all the different media companies you’ve worked on and studied. I always enjoy our chats. So, it’s fun to be able to do on live and record it. So thanks for doing this.

Alexis Grant: Yeah, of course. You’re always easy to talk to. So thanks for that.

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