Alexis Grant on Launching They Got Acquired

Jacob Cohen Donnelly: On your about page, you say that you launched They Got Acquired because you had gone through two exits in six years and realize there were no good resources for entrepreneurs like you, AKA, those not trying to build unicorns. Can you talk about your media career and how it set you up to create They Got Acquired?

Alexis Grant: Yes, so my first exit was a content marketing agency and it was a small exit. This is the first time I really started running a business. My background is in journalism. After I worked in journalism for a few years, I got the bug to start running my own thing, and I started. I started as a freelancer, like many people do, and turn that into a small content marketing agency. That ended up being acquired by one of our clients. At the time, we ran blogs for other businesses. This was in like 2010, from 2010 to 2015.

One of our clients was a site, a personal finance site called The Penny Hoarder. We were running the content for that site. We didn’t start it, the founder started it, and he came to us after he realized that he wanted to spend more time on the business, and less time thinking about the content. We worked for him for about a year and a half before he acquired, that company was an aqua hire, which means that he brought myself and several members of my team and our processes for creating content in-house there so that we can focus on growing the content operation at The Penny Hoarder.

I stayed there until 2019, and we can talk more about that, but it was a really great experience, getting to scale a media company. It was also bootstrapped. Everything I’ve worked on has been bootstrapped, but the company did very well. We had a lot of resources and I got to learn how to build something that was much bigger than I was doing on my own. When I left there in 2019, I picked up another project that I had.

I started years earlier when I was running the agency as a side hustle or a little side project that the agency was running, and it was called The Write Life, it’s a website for writers. I picked that up after I left The Penny Hoarder. I was in a transition, trying to figure out what I want to do, did I want to work on it? I ended up working on that business for about a year, not full time, but just dabbling it here and there, trying to figure out if I wanted to spend more time on it, and decided, in the end, to sell that company, so that was in early 2021.

Going through both of those experiences of selling made me realize that, yes, there’s not a lot of resources for entrepreneurs that have six or seven-figure exits and I wanted to help fill that gap.

Jacob: The Penny Hoarder, obviously, acquired for about $100 million, I don’t know the exact numbers out there. You spent nearly four years there, and the team grew from you being the third person to there being over 100 people on the team. What did you learn from experiencing that really fast growth in a pretty short period of time that hasn’t formed your strategy with They Got Acquired?

Alexis: Yes, just because we’re throwing around a lot of acquisitions. To clarify, that company was purchased by a public company. The Penny Hoarder was purchased in 2020 and that was actually after I left. In the years prior to that, I was there from 2015. Well, I worked with the founders since 2014 and I left in 2019. What did I learn while I was there so much? Part of that was realizing what I like most about scaling and what I don’t like, and where my strengths fall. I got to do a lot of the infrastructure building in the early days, and I realized I really enjoy that.

We did strengths finder at the company which I came into that being a total skeptic, I’m not really into like with all these personality tests, but I did it. There was a real learning for me there, and that one of my top strengths, my top strength was futuristic, which makes sense for an entrepreneur, but then my second one was a ranger. What that means is I like to put the pieces in place to help other people succeed. Prior to that, I hadn’t really thought of that as a strength that I could lean into.

I hadn’t really thought of it as– like I knew it was, vaguely, I knew I was good at it, but once I put my finger on that, I really leaned into that. I got to focus on a lot of our infrastructure in the early days, a lot of hiring. I helped to grow our content team, so I was getting the right people in the door, figuring out what everyone would do, what was our process for creating and publishing content? Including, distribution and SEO and the marketing pieces, and how did that all work together?

I think that was the biggest piece. It’s just getting to go through that process and learning along the way.

Jacob: Let’s lean into They Got Acquired and talk about really what you think the long-term business here is. Because I think what’s really fascinating about this is nobody we talked with at the top of the show, nobody talks about this type of business acquisition. It’s either Mark Zuckerberg and becoming a multimillionaire or it’s nothing. There’s nothing really in the middle, which is the vast majority of these businesses. What is the content strategy for They Got Acquired, and how do the various pieces of content that you’re creating fit into a broader strategy for the business?

Alexis: On the front end, we’re a media company, and that’s really what my strength is, and one of the reasons why I wanted to build it. We have content around– we tell different stories of different entrepreneurs who have built businesses and sold them and how they did it, and then we also offer resources. For example, we have a post that went live recently about mistakes you don’t want to make in your first LOI, your first Letter of Intent. I think a lot of the content we can provide that’s tactical will be really helpful, especially to first-time sellers who are going through the process for the first time.

Because when you’re building your business– a lot of people who end up selling their business, they might not have that in mind from the beginning, especially first-time entrepreneurs, it’s different, it’s either second or third time. You’re building your business head down. You’re not thinking about how to sell a company, you’re thinking about how can I make this business sustainable and profitable. Then suddenly, you have an opportunity to sell and there’s a real learning curve, you have to learn that really quickly. Our goal is to help those entrepreneurs get through that time.

We have content on the website, we also have a podcast, and that’s purely stories from founders. At least at the moment, I get a lot of pitches from experts who want to talk about acquisitions, but at the moment, it’s a really storytelling narrative-type podcast. Then, on the back end, we are building a database of all these acquisitions. We have more than a thousand that we know fit our criteria and our criteria is pretty simple. The business has to be primarily online, so we wouldn’t cover a brick and mortar.

It has stuff sold since 2017, and the deal price has to be between $100,000 and $50 million, which is a really big a huge space to play in. Some people would say I think the six and seven-figure sales have more in common than some of the eight-figure ones, but I think there’s something we can learn from all of those. Our goal in terms of monetizing this is to use that database and sell the insights that we get our hands on through the database, which is new for me because I’ve done a couple of different models for monetization.

At The Penny Hoarder, we did performance marketing, so sending leads to our clients. I’ve done a lot with affiliates, and obviously, sponsorships and advertising is always a great option in media companies. I’m really interested personally in taking the data route and being able to sell reports that are based on the data that we collect.

Jacob: I want to talk about revenue a little bit but you launched your content marketing blogging agency, probably about a little over a decade ago. I remember when I was first getting started building blogs and stuff was at a similar time. Growth, at that time, looks very different than it does today. The things we did back then to get people to visit our sites, the tactics we tried, they’re just different. What have been the early priorities for you now in 2022 to grow the audience for your site that is probably different than what you were prioritizing, say, a decade ago?

Alexis: Yes, that’s a good question. To be honest, this is one of the things that I think always makes growing a media company challenging, is even if you’ve done it before, you haven’t done in this moment in time, and this moment in time is different than the last moment in time that you built something. On a day when I’m not feeling as confident, I might say to myself, “Could I do this? Yes, I’ve done it before, I booked a few companies,” but I haven’t built it in this moment in time and there are certain challenges about right now.

We only launched in February, and the things we focused on initially have really been very scrappy, and a lot of it has been based around me. I have a team of about 12 contractors right now. Most of them are doing the content pieces and I have someone now who I’m training up on some of the more growth strategy parts, but initially, it was really just outreach and trying to get people one by one onto the email list. One thing that’s different is I think years ago, when I was building The Write Life, for example, I always had an eye on website traffic.

I have barely checked the website traffic since we launched. I don’t really care what the website traffic is now. My husband and I were talking about that today. We went on a hike this morning and he’s like, “What’s everyone doing on the website?” I said, “You know what? It just hasn’t really been my priority. The website.” I want people to convert over to the email list. That’s what I have my eye on, is whether they’re converting, but our number one KPI really is email.

That was always important, but I think– I’ve learned through the years, the importance of having one north star, and so knowing from the beginning that that’s our north star has allowed me to help keep our team focused on that.

Jacob: Is the primary promotion of the newsletter the call to action on the website? Have you experimented with lead magnets or various other sorts of ways to get people to sign up or is it really a prominent call to actions on the website right now?

Alexis: We will have more ways of getting onto the email list, but we haven’t really done much yet. Right now, it’s just the website and through the podcast. Now, that the podcast launched, we’ve had four episodes so far and we have an ad in the podcast for ourselves, for the newsletter. We sold a few sponsorships but rather than fill that entire sponsorship slot with paid sponsorships, we opted to use some of the inventory to send people to our newsletter.

Jacob: Let’s talk about revenue because it seems as if right out of the gate, you’re already making money or at least generating revenue. I imagine it’s still a new business, profitability takes time. On your advertised page, you talk about sponsorships tied to your newsletter, to your podcast, you mentioned reports. Can you talk in more detail about the various products that you’re offering to partners? Then also, how do you decide on what to charge for them? I find for people who are launching their first media company, this is one of the hardest things to figure out, is what do I charge for an ad? How do you do it?

Alexis: We’re still super new, so this is all involving as we speak, but I can tell you what we have at the moment is we have a newsletter and each newsletter has one sponsor and they have a logo at the top, and then they have a sponsor message in the newsletter. We launched out of the gate with one newsletter a week, and we just increased that to two a week. Partly because I realized that we already have plenty of content to do two a week. For us, I don’t think the right strategy is to have this super long email.

I want to have shorter emails that give people the information they need really quickly and so I would prefer to have two a week than one a week, and it also gave us more inventory for sponsorships. We just move to the two a week. We also have the newsletter and then we’ve already finished recording this season of the podcast, our first season, but for the next season, which will probably be in the fall, I don’t know the details of it yet, but it looks like it’ll be in the fall, we expect to sell sponsorships for that podcast.

We’ll probably sell it for the whole season, just to make it easier on ourselves. Then, I also expect us to have other opportunities for advertisers. When our reports start being watched, so just to back up for a second, some of the insights that we hope to release from the database. I can give some examples. When I was selling my content company, I wish I had examples of other content companies that I’ve sold, so I would love to allow other entrepreneurs to download reports of, say, 15 content companies that sold last year for 6 or 7 figures.

You can look at all the metrics around those other companies that are similar to yours and think about how yours might fit in there, like real estate comps like you do for your house. I could see a world where a sponsor might want to sponsor that. Another product we’re working on is companies that buy SaaS companies. If you’re looking to sell your SaaS company, these are some of the PE firms and other companies that you might want to pitch and tell them that you want to sell it to. Those are some of the products that we have not released yet but we’re working on them.

When they come out, we’re hoping that some of them will be paired along with the sponsorship. In terms of how do we price them, it’s a shot in the dark at the beginning. My barometer is if people say no, then it’s too high, but I started out with a $5,000 sponsorship. When we launched, we had about 1,000 people on our email list because ahead of launch, I had worked with just a simple landing page to try and get people on the email list. At launch, I offered a few sponsors of $5,000 package.

I can’t remember exactly what it looked like, but it was a few newsletters and one or two podcast sponsorships, which sounds like a lot now to me, but at the time, we only had 1,000 subscribers, so we didn’t have a huge list to work with. What’s really interesting though is it’s new to me to be in a space where– I think this is a good space for sponsorships. I compare it to The Write Life, where the writing industry is very different. Writers don’t have a ton of money, and therefore, a lot of the companies that serve them, they have to get a lot of customers to make it worth their while.

If you look at this space I’m in now, first of all, there’s lots of companies that are really eager to get in front of entrepreneurs, especially entrepreneurs that are thinking about selling their businesses, while they’re talking about wealth management. All these marketplaces, M&A advisors and brokers, they’re all itching to get in front of this audience because there’s certainly not another content company like ours that focuses on this particular moment in time for a company, the acquisition moment.

A lot of the information or the content that’s online around acquisitions comes from the brokers or the M&A advisors, the people who are in there themselves. They have a dog in the fight or they’re more of a third party, where they can use us to reach the entrepreneurs who want to sell. What I’m saying is, I think that there’s a lot of opportunity here for sponsorships because these companies really want to reach these entrepreneurs and we can help them do that. For one of these companies, if they get, say, one client or one customer through our newsletter, that can be really valuable for them.

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Jacob: Big debate over the past couple of years has been the advertising versus subscription one. Right now, at least, you’ve put yourself on one side of that debate by going with advertising. Why did you opt for an advertising first approach? Have you thought about subscriptions? Again, I understand the business is two months old and I’m asking a lot of questions that are perhaps forward-thinking but I’d be curious to know your thinking here when so many newsletters and so many publications we’re launching subscriptions first, you opted to go ad first. I’d love to understand your thinking there.

Alexis: I actually consider myself to be going database first because the database is how we want to monetize long term. From the beginning, I’ve thought of the sponsorships as secondary, but because I’ve noticed since we launched just how much opportunity is there, I’m going to dial it up a little bit to help us pay for the site until the database report can be released and start making us money. The reason why I wanted to do this instead of go the sponsorship route is that quite frankly, I think it’s more fun to have free content like content that’s available to everybody in front of a paywall.

You can reach so many more people, or as if you’re behind a paywall, your growth opportunities, you can do– There’s tons of people succeeding at this, but you have to grow in a different way because there’s a lot of things that I think you can do if you have a lot of free content in front of a paywall that you can’t do if it’s only a smaller number of people reading something behind a paywall. In terms of growth, I think it’s easier. I personally, a lot of my experience has been growing through free content.

Maybe eventually we’ll put something behind a paywall, whether it’s a newsletter subscription or we might have a subscription membership option on our site, where you can only see a certain number of content pieces before you have to pay. I don’t know. These are all things around the table right now, but my preference is to grow with free content and get that brand that foundational, like people love the brand, people are loyal, they’re into what you’re doing, and then launch a paid product.

Jacob: Going back to the reports, will the reports be primarily sponsor-driven or are they going to be paid reports where like, if I want to understand the 19 companies, the content companies that sold over the past two years between a million and 10 million, is that something that I’m going to fork over my credit card for?

Alexis: We have a couple of ideas here. For one, I do think that entrepreneurs who are going to sell or want to sell their company, it would be helpful to them to be able to see comps of other businesses that have sold. I mean, big businesses do this already. Huge companies have that type of information at their fingertips, but no one’s gathered it for these size companies. Then, eventually, I’d also like it to be able to be more customized. I can see a world in the future where you might have a subscription or a membership to the site and be able to log in and pull your own report.

Say, “Hey, I’d like to see this type of company that sold for this amount that had this many page views or had this many email subscribers,” or whatever’s important to you and be able to filter through the data on your own.

Jacob: Well, that makes a lot of sense. I think there has been a real big push over the past few years for companies to use content, to acquire an audience, to then push into data place in some way. I wrote about it. I want to say it was six or seven months ago. Just because I think it’s really a fascinating area to play in.

Alexis: The interesting thing here is, because I’ve been thinking a lot, and I’d love to write a blog post about this at some point when I can find the time, but I’ve been thinking a lot about how so many content companies create the content, but they sell something else. In addition to running a content operation, you’re also having– if people aren’t paying directly for the content, you’re also having to run the other operation of like what you’re making or selling or layering on top, whether that’s a course or– I mean there’s a million different ways you can do it.

But many of the content businesses work that way where the content is free on the front end and funnel people toward them. What I like about what we’re doing is there’s so many synergies by covering the stories of entrepreneurs who have sold where building the front end of our media company, where also populating our database at the same time.

Jacob: Kill two birds with one stone.

Alexis: Yes.

Jacob: I want to talk about your team a little bit. You have these great company cards that I think are our core part of every story you’ll put the deal terms on the left side and you have your own. That says you have a team of 11, although you’ve been through 412 contractors. When you were at The Penny Hoarder, you built this giant team of 100+ people and all that. Probably a lot of them in-house. How have you thought about the benefits of taking a freelance first approach or is that only in the beginning, but at some point, you’ll pivot and start bringing people in-house?

I’d love to understand your thinking about that, especially as you’re building this bootstrap business, where at the end of the day, you have to pay the bills until the thing’s profitable.

Alexis: I mean the primary reason I have freelancers and not employees is because I’m bootstrapping. Also, I believe in a remote-first environment. I think you can get the best people when you have a remote-first environment. Some writers like to be freelancers too, especially when you’re thinking about like writers, reporters, and editors. For a site like what we’re doing, diversity matters, like having different voices of perspective, even though they’re basically writing news stories. It helps to have a number of different bylines because I have different people with different backgrounds coming to the stories.

I actually wouldn’t want one person writing all the stories right now, even though that would be more efficient. It’s on purpose that we have a portfolio of writers because they bring their perspectives to the piece. My eventual goal is I could definitely see a world where we have a few employees. I have no ambitions to build a huge company. I’m not interested in that. It’s the ethos behind They Got Acquired is you don’t have to build a huge company to do really well. Do I want to bring it a lot of revenue and a lot of profit? Yes. Do I want to have a hundred people on my team? No.

I have long been amazed and fond of the model of having a small team people-wise that can do really well revenue-wise and also in terms of impact. Initially, we’re starting out with freelancers. My hope is that once we’re making more money, we can bring in a couple of employees, but I suspect we’ll always have both some employees and some freelancers

Jacob: The bulk of those people are focused, at least based on the company page, exclusively on content. You don’t have, as far as I could tell, anybody focused on the “business side of the operation”.

Alexis: No.

Jacob: Can you talk?

Alexis: Yes. Since I’m bootstrapping, I’m thinking about what are the easiest things to delegate. For me, the content operation is the part that comes, it’s not easy, but it feels fairly straightforward to me. My background is really in building content teams. What I’ve done is I’ve built the content part of the business where, it can’t all run without me yet, but even just a few months in we’re getting there. Some of the pieces are running without me, which is helpful so I can think about other things. We have a handful of reporters– and I don’t think the About page. It’s missing a couple of people right now.

An editor, we have a podcast producer, a designer, and I have an operations manager who’s helping with, they keep things moving. What I would love to hire for is someone to help with audience growth. You asked about the side of the business side, I’ve basically been doing that. For me, it’s more about like, how do I balance– when you’re bootstrapping, you have to think about what’s the most important thing to put your money into? There are things I can do, but I shouldn’t do, but then you have to really think about like, how do you spend your money?

Right now, I’m spending about $12,000 a month. My goal, by the end of the year, I’d like to be covering all of that expense. On our way to profitability, but I’m not pulling a salary right now myself.

Jacob: I want to spend a little time talking about the technology stack because you put out this great pie chart about the costs to launch the business. I think it said something like $31,000 to launch the business of, which the largest chunk of that was content. I think $12,000. Then. I think the next largest chunk was the website. I’d love to understand what the technology stack is that powers They Got Acquired.

Alexis: It’s really simple, which is what I love about building online businesses. It’s just knowing what tools you want to use. We use WordPress, but we built a custom theme. This is one of the benefits of having built a number of content companies is I know exactly what I want on the backend. I’ve worked a lot with SEO, for example. There are features that we want to have on the backend that don’t come in and out of the box theme. Like for example, I want to be able to update a dateline instead of just having the dateline for each story.

When we update a story, I wanted to say updated.

I also want to hide it from the Homepage because I don’t want it to pop up on the Homepage necessarily every time, like if we update it. There’s little things that we are able to build into the theme, which is helpful. We use a convert kit for sending our emails, which has been great. I’m hoping that that will scale with us. I think it’s not necessarily the preferred ESP for big media companies. We’ll see, but I love the simplicity of it. I also love how easy they make it to create autoresponders and sequences. We haven’t done a lot of that, but we will, we were in the middle of building some of that out now. What are the tools I’m going to tell you about? Are there any, in particular, you’re curious about?

Jacob: I’d love to know, you’re talking about this database that you’re building out, I’d love to understand how are you going to build that because that could be a massive undertaking if the overcomplicated or whatever?

Alexis: Yes, it’s an Airtable. This is my first time using Airtable, so that’s been cool because I’ve gotten to learn a new tool. I’ve really enjoyed that.

Jacob: I’ve used Airtable in the past. It can do basically whatever you want. It’s like a fancy Excel sheet with a ton of logic. Anyone from Airtable listening, thanks for a good tool.

Alexis: It’s funny because my husband is a Google Sheets expert. He sells courses on how to use Google Sheets so we do everything in Sheets in my family. It was a real jump to push over to Airtable, but I found it to be, this is complicated– I started the database goes, I suppose it’s not that complicated but there are tons and tons of fields, it’s way too complicated for a Sheet. It’s been nice to be in there.

Jacob: The publication is a few months old. You’re still figuring out what works, what doesn’t work, and all of that. When we talked at the top of the episode, you’re not new to this. You’ve launched multiple things before, you were at The Penny Hoarder where it grew from 3 people to 100+, revenue grew considerably, the content operation grew considerably. When you were planning to launch before you even hit publish on day one, what were some of the things that you felt were absolutely critical to launching the business effectively?

Alexis: Number one, email list. That’s why I put a Landing page up as soon as I was even– I wasn’t even positive I was going to do this and I put a Landing page up because I wanted to, first of all, test, if anyone cared. Then if they did care, I wanted to collect their email from day one, so that when we were launching– When we launched, we didn’t launch to crickets and that really helped a lot. In fact, we’ve gotten some great coverage, we got a story in the New York Times. That was really because I had built the email list ahead of the launch.

It was only a thousand people but there were some great people on there and they cared about what we were doing. That was the first piece. High-quality content to me is a given and probably is to anyone listening to this. I think for people who aren’t content first when they’re building a media company, it’s worth noting, it’s just how can the content be really good. I put a lot of thought into that because, especially right now, credibility is so important online for media companies. There’s so much crap out there that if you don’t gain people’s trust from the beginning, then it’s gone.

For example, one of the things, one of the features we have on the site is if you look at the bottom of any story, there’s a little sources pop out. You can click on the sources and it will pop out and show you the sources that we relied on for that story so you can see where we got our information from. We really try to be transparent about, “Here’s what we got firsthand, here’s what we got from someone else,” just letting people know.

Jacob: Right now, very much zero to one. Let’s fast forward a few years. Let’s put the dream hat on, the ambition hat on, the where I want to be hat on. In three to five years, where do you want to see They Got Acquired?

Alexis: I want us to be the number one place people go if they’re thinking about selling their business or if they want to build a business that will eventually get acquired. Right now, we’re focusing on the moment of acquisition, but I think there’s so many learnings in there for people who want to build a business that will get acquired in three or five years.

Jacob: Are there specific products that you imagine expanding into? Do you think it will look similar to what it is today?

Alexis: I’ll say I’m pretty good at rolling with it because even though I have ideas– An example, I mentioned earlier that I’d love to have a membership login where you can log in and sort through the data yourself. That’s one thing I envision. Already, a few months into this, there are things that are different now than I envisioned them at the beginning. I try to really stay open-minded and not think too far ahead because I know that things will change.

Jacob: I want to end with the same two questions that I ask every single operator that comes on the show. First, what is a mistake that you have made in your career that you wish you hadn’t and what did you learn from it?

Alexis: Not firing fast enough. One of my favorite parts about doing this is growing the teams. In fact, I often end up working with some of the same people for my next project that I worked with on the previous project. I love watching those people grow and going on to get new opportunities. I think because of that, I have made the mistake of letting people stick around for too long when they were bringing down, not only themselves but the team. I’ve gotten better at that over time. It’s an important skill.

Jacob: Then, what is some advice you would give someone who is thinking about launching their first media company today?

Alexis: Think about monetization from the beginning because I think a lot of people that start media companies, they love the content, they love the storytelling, they’re into the content part of the business. When you start, sometimes it makes sense to say, “Let me start this, and then I can see if I can make some money off of it.” If you really want it to be something that’s going to sustain you and your family and an entire team, it makes sense to come in from the beginning knowing how you’re going to make money.