Len Markidan on Building a $5mm+ ARR Startup with Content Marketing


Today, I’m talking with Len Markidan, the Head of Marketing at Groove, a SaaS startup that makes hassle-free customer support and engagement software for small businesses. 

Len has been with Groove since the very beginning and he attributes much of their success today to their execution of an effective content marketing strategy. 

Content marketing has been all the rage for startups the past few years, but so many startups have invested time and money without seeing results. However, this isn’t because content marketing is dead, it’s because most people don’t approach it with the right mindset and today, Len is here to set the record straight.

In our chat we cover how Groove struggled to get traction early on, what it was like to spend 6 months rebuilding the product from the ground up only to launch to crickets, and how they turned things around and built a $5 million dollar ARR business on the back of content marketing.

If you’ve struggled to get content to perform for your startup, then this is the podcast for you.

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Topics covered:

  • How Groove found its “groove” (I’m sorry, I had to).  (1:22-4:08)
  • A new approach to marketing.  (8:08-12:15)
  • You’ll be amazed how many people are willing to help you.  (20:38-22:07)
  • You’ve got your content out there, now what? (25:33-31:09)

Resources mentioned:

17 Email Scripts To Grow Your Business
We Hired A Business Coach, and Here’s What Happened

Where to learn more:

To learn more about some of the tests and strategies that Len and his team have put into action and follow along on their journey to $500k MRR and beyond, check out Groove’s blog.


Andy: Len, thanks so much for coming on the show.

Len: It’s my pleasure and an honor.

Andy: So today Groove is at nearly $500k in MRR, but when you came on board, things weren’t looking so rosy. What were things like when you first joined the company?

Len: So I was there in the very, very early days, right after the initial prototype was built. There were only a handful of beta customers. I wish I could tell you that I came in and turned everything around, but the reality is I was there for quite some time. We were doing a lot of things – I was doing a lot of things as well – that weren’t working very well.  We were at around $250k in MRR for around 8 or 9 months, and really just had a lot of trouble finding traction. We were trying a bunch of different things, we tried some really bad content marketing, we tried some PR. It’s one of those things where we tried some things and did a really bad job at it.

Andy: I know exactly that feeling. It’s like I’m reading a blog and it’s telling me about this new channel, let me try it out. I give it a half-assed effort and don’t know what I’m doing, I decide it’s worthless and I move on to the next one. That’s not exactly how it works, though. So what happened, what turned things around to change your mindset?

Len: The reality is, we had our feet to the fire. We were pretty much looking at 6 months of runway or so, and had this product that we knew could solve problems for people. It was a sellable product, but nobody was buying it. And we really had no other choice other than we knew that what we were doing wasn’t working and we needed to do something that would work. So we had a meeting and said “what do we do?” We spent a lot of time trying to figure that out.

One of the things we kept coming back to was content marketing. Because we would see a lot of SaaS companies just crushing it with content. Companies like Hubspot, they were building real businesses just on content marketing. And we had “tried” content marketing, we put out a bunch of posts like, “9 Reasons You Should By Groove”. It was garbage, it was terrible, nobody would read it because it was really, really bad. We didn’t understand our audience, we didn’t understand what the real challenges and viewpoints were, and we got the results that we deserved.

But we were looking around and we were saying, hey, these companies seem to be winning in content marketing, so we just reached out to people – the team at Hubspot – and asked if we could chat and take 30 minutes of their time to learn about what’s working for them. Surprisingly, people were very generous with their time. People talked to us and what we learned was there was a massive amount of sophistication going on under the surface. The strategy that these companies would deploy, the deep understanding that they had of their audience, we just weren’t approaching anything near that.

So the turning point for us was realizing all this stuff that was going on under the surface. And at that point we basically took our blog down for 2 months and spent those 2 months doing nothing but research and talking to our audience, figuring out what we were going to do next for the blog, planning what would eventually become our journey to $100k in MMR blog that pretty much ended up saving the company.  

Andy: So what did these early conversations with your audience look like? Do you just email those early users, what are you doing to talk to the audience, how does that whole process work?

Len: That’s a great question. We would just email our users and ask if we could chat for 5 minutes on Skype. And again, just like with reaching out to the people that are doing really well with content marketing, it was surprising and amazing just how willing people are to give their time. It’s probably one of the most underutilized strategies to just ask people to help you. And you will be amazed at how many people are willing to help.

We would reach out to customers and people who were former customers. We had 1,000 people in our initial private database, and of those, 20 people became customers. And we reached out to those other 900+ people and asked if we could chat for a little bit. We would ask them questions like, “What are you struggling with right now?”, “What’s really tough for you?” “What do you wake up every morning thinking about when it comes to your business?”, “What are the real thorns in your side?”

And one of the things that was interesting was we knew our market was small business startups, but when we phrased problems this way – Groove sells customer software support – but when we phrased questions this way, almost nobody mentioned “customer service”. Most small business owners don’t go to bed at night thinking their customer support isn’t streamlined.   

Andy: It’s just not a real concern.

Len: Exactly. It’s not a real pain point for people to the point where if you ask them what their real pain points are, that’s totally not top of mind. What we found is people were struggling with a lot of the same things that we were struggling with as a startup. They were struggling with cash flow challenges, they were struggling with hiring great people, they were struggling with operations issues and growth and marketing and those sorts of things. And that’s where we got the idea that we’re a startup going through all these same problems and challenges, what if we wrote about our own experience going through those problems and tried to help other startups and small businesses that are tackling the same problems. Wouldn’t that be a little more interesting and useful to them than going after customer service issues that they might not even really care about.

So we weren’t really targeting customer service professionals at massive organizations that are customer service executives that need all this help, quite yet. We were targeting small business owners, founders, C-Suite. We were a very small scrappy team and they just didn’t have the time to really think about customer service.       

Andy: They’re not trying to optimize customer service operations.

Len: 100%. They’re just trying to either survive or grow. And those are the same challenges that we were facing and so we figured let’s get in front of these people by solving those problems for them first. And then when it comes time for them to grow into customer service software and to buy some, we’ll be the no-brainer.

Andy: So it seems like when you had these conversations with content marketers getting results, when you reformulated your approach, the first step was to figure out what your customers actually care about. I’m guessing there’s a little more to the process than just asking your customers some questions and writing some articles, and then headed on a rocketship to $500k MMR. What happened next after you started putting out this new content when you relaunched the blog, what happened?

Len: So one of the things that we kept hearing over and over from the smart people that we talked to was, if you build it they won’t do anything. If you build your content, they’re not going to come read it just because you built it. You have to actually get it in front of people’s faces. That was something that was very top of mind for us when we relaunched this whole thing. We knew that we didn’t have an audience, we didn’t really have this built in list of thousands of people. But a lot of other people had many months or years of cultivating and building trust with hundreds of thousands – or even millions – of people. And we knew that if we could get in front of those people that we could expose Groove and our content to a huge new audience.

That’s really what our strategy centered on. We built some content and then we started reaching out to people, and we did it in a way that was unlike anything we had seen in our research. There’s this whole field now of influence or outreach, it’s this massive marketing wave for consultants to make money. And it’s called “influencer outreach” and it gets a bad name because most influencer outreach is terrible. It’s total garbage. People who are influencers will get multiple emails a day that look something like this, “Hey Andy, I just wrote this post and would really appreciate it if you tweeted it out for me.” Who would respond to that? Nobody at all cares about that, that’s an instant delete.

We tested a bunch of different scripts, we sent about 40 different scripts to hundreds of people, and what ended up working really well for us was just taking a much more personal and grateful approach. We say something like, “Hey Andy, I saw that post that you wrote about email subject lines. I thought it was really amazing – and in fact – we applied it to this email campaign that we sent out this morning that saw a 10% increase in opens just from that one piece of advice.” So fact #1, you’re taking much more time to write this email, but you’ll get 10 x’s the results.  But if you keep it personal and make it clear that we know who this person is, and we not only engage with their content, but we use it to succeed because that’s ultimately what people want.

So we say, “Thanks very much”, we show them how we use their content, and then we would say, “I wrote a post with some interesting test results around some subject lines that we tested.  There are a couple of words that we found that we changed and it gave us a 40% increase in conversions.” So we give it a compelling teaser, and then you say, “I know you’re an expert on this, and I really appreciate your feedback. Do you mind if I send you a link?” So what’s happening here is you’re not saying “here’s this post, go share it”. You’re not even saying,” here’s this post give me feedback”. Your “ask” is for feedback, it’s not for a share, which is totally different than what most people will ask. Instead you’re saying, hey, you know that expertise you spent your entire career cultivating, that you’ve dedicated your life to, your passion? I value that a lot more than you going and tweeting my post right now. That, to me, has a ton more long term value. And that’s a level of respect that 99% of marketers will never pay

Andy:  And you’re also asking for permission before just ramming the URL down their throat.

Len: 100%. I’m glad that you caught that. That seems really subtle to a lot of people. You’re very smart, but I know a lot of people that haven’t done this kind of stuff before. It seems almost like a throwaway, that subtle doesn’t matter. But that’s actually massively important. And the reason it’s massively important is that it fundamentally changes what you’re asking for. You’re not saying, “Here’s this project, spend 15 minutes on it.” You’re asking a question that has either 3-letter answer – yes – or a 2-letter answer, “no”. And that’s an incredibly easy ask.

And it’s almost harder for them to say “no” to this.  It’s almost more work to say, “no”, then they feel like they have to explain why. But if they say “yes”, that’s just 3 letters. And with a tiny ask, it’s so easy to get a simple “yes”. But it’s also a lot easier to get a big ask after you’ve gotten a small ask. So what typically happens here is they’ll say, “Sure, send it along”. And then one of a couple things will happen.

One, they’ll give you feedback, which is amazing, because now you have feedback from an expert that will make your content better and more useful and more interesting to people. And now they’re in the creation of your content, so of course they want to succeed. They’ve helped develop it so it’s in their best interest to make sure it’s successful, so of course they’ll share it with their audience.

Or number two, what we saw happen a lot more often than one might think – and certainly a lot more often than we thought – people wouldn’t give us feedback on it, but because we had taken such a different tact, they would just share it anyway.

Andy:  So when you sent it all over to them you asked for feedback. If they reply with it and give feedback, do you then say, “Will you help us share it?”, or is it more you don’t ask?

Len: You definitely can ask, you very rarely get what you don’t ask for. But what we’ll typically do is we’ll incorporate this feedback. But we’ll use their feedback to actually make the post better, and then we’ll come back and say, “Hey Andy, thank you for the really useful feedback. We used it and incorporated it into section x and y, and I really think this makes the post a lot stronger. Thank you for taking the time, I really appreciate it. I just pushed the post live and would really appreciate a ‘share’ if you wouldn’t mind.”

Andy:  Ok, so it’s just a simple ask at the end of that. But you’ve responded to the feedback, acted on it, and keep it simple at the end of that. Now I know this question misses the point a little bit, but I do want to think about the specifics. Ideally what sort of ‘share’ are you trying to get?  Ideally is it just a tweet, or do you want something deeper than that?

Len:  That’s a great question. And we would actually play with the calls to action in the emails. So in some of them we would ask for tweets, some of them we would ask them to share with their email list, and some of them we’d ask if they would actually go and comment on the post. The reality is they delivered different results to us. There’s not really a hard and fast rule that I could give. I could give a practical tip and say always ask for this kind of thing. But it really depends on who you are.

What was really helpful, for example, in our first post was to ask people who helped us to comment on the post. Then when people come and see the post, they see that Gary Vaynerchuk left a comment on this post. This is validation. This is clearly some heavy hitters validating the content, so I should pay attention and read it. Later on maybe the value proposition changes and maybe you get more value out of the actual distribution than validation. And you ask people that you know have engaged email lists to share it with their lists, and ask people that you know have big Twitter followers to share it on Twitter.

It’s really contextual. It depends on what your goals are, who the actual person is, and where their biggest strength is. I would encourage you to play around with it. Make different asks and see what works best for you and what people respond to. Ultimately, none of the actions that you ask for are going to hurt you.  

Andy:  Right. Especially at this point, you’ve shown you’re already different, you’ve shown a more thoughtful approach. So by just saying “Twitter” instead of “email list”, in your ask comment, that’s not going to be the make or break thing in the whole process.

So I’m curious. Backing up a little bit, when you plan out a new piece of content, you’re building this distribution, this promotion, into the entire process. So how far in advance before are you publishing the piece of content do you need to start reaching out to people?

Len: That’s a great question. In the early days we would have these about 3 weeks in advance, and we would have essentially a 1-2 week push where we would just try to pull up as much feedback from as many smart people as possible. And then we’d have another 1-week push where we’d reach back out and take the time to incorporate the feedback, and then we would send it back to people and say it’s going live the next day and would really appreciate a share.

After we push it live we would send an email to people who had given us feedback, and we’d say thanks for the share, we really appreciate it.

Andy: Ok, and how many people roughly – I assume it’s always a different based on the type of content you’re promoting – but how big of an audience of influencers are you contacting. If you look at the standard bad content marketing, they’re sending URLs to hundreds of people, anyone they can find an address for. I guess that’s not the approach you take, but how wide should you be shooting?

Len: That’s another good question. So we originally targeted around 80 different people when we first launched the blog. But here’s the thing, you’re not going to build a long term relationship with 1,000 influencers. You’re just not. You don’t have the bandwidth as a content marketer to build 1,000 long term relationships with people. But what we found is having those long term relationships has benefitted us massively over the last 3 ½ years since we launched the blog.

So of those 80 people who helped us originally, we have super deep relationships with about 25 of them now. And we have what we call the “Groove inner circle”, and they are basically just influencers who we send content to before it goes up and they are happy to give us feedback. There’s a feeling of exclusivity being around the first people to see that content, but also in helping us develop it.

But those people have created insane amounts of value for us over the last 3 ½ years by sharing our content, by helping us make our content better. And that’s just so much more useful to build those relationships and have those relationships long term, than it is to spam 1,000 people and play the numbers game where I have 1,000 people and maybe I’ll get lucky and 25 of them will share the content, but they’ll also be annoyed and never want to hear from me again.  

Andy: For sure. And to play “devil’s advocate” a little bit for the members of the inner circle, what’s in it for them?

Len: That’s a great question. So, a couple of things. I wouldn’t discount the feeling of ecstasy. A lot of the things we do is just the psychology of it and because they reinforce the story we tell ourselves about ourselves. So if they see themselves as influencers, if they see themselves as content marketing experts, if they see themselves as gurus in this field, then this totally matches their story to be part of this exclusive inner circle where we already have somebody – like Andrew Warner – and they also want to be in that group because that’s the kind of person they see themselves as.

And then it just goes back to people who are successful, they’re often much happier to give back than you would think. We found this to be a theme over the last 3 ½ years, which I mentioned 3 different times in 3 different cases already today, where people have helped us build better content, people have helped us share stuff. A lot of people leave insights and leave really valuable help on the table just because they never ask for it. I promise you, if you just ask for help in a way that’s thoughtful and that respects the person’s expertise and time, you’ll be amazed at how many people are actually willing to help you.

Andy: I found that myself, too, especially in doing podcasts and all of that. If you can make it clear from the beginning that you’re giving personalized effort, that you’re actually going above and beyond. Because when I reach out to you and anyone else, I know you’re busy, so I do my best from the very first contact to make it clear that I’ve put in some homework and I’ve done my research to show that I’m not spamming anyone, I’m trying to set myself apart a little bit. But I’ve been blown away by how helpful people have been.  

So I’m curious, after you’ve done a lot of this outreach and you’ve gotten this content out, is it just onto the next content or is there more that needs to be done with whatever article you just put out?

Len: So a couple things. First I really want to repeat a point that you just made, which I think is really important. When you send out an email to somebody, you make it clear that you did some extra work. That is surprisingly the biggest differentiator between people who get help and people who don’t. People who get help did 5-10% more work.

In a world where almost all influencer marketing emails look like spam and they look terrible – because almost all of them are spam – doing a tiny bit of extra work, just a little bit of research on the person and say something thoughtful that’s personalized to them. That will set you apart in a huge way. And it doesn’t take that much more work, it just takes a little bit more time. But that’s more time than 99% of people are willing to invest. That’s why if you do that, you set yourself apart from the rest.

Andy: Just so listeners don’t’ get confused – and hopefully they wouldn’t – but going back on someone’s blog and finding the most recent title and copy and pasting it in an email, that’s not really what we’re talking about.

Len: No, you’re totally spot on. And that’s why the word “thoughtful” is really key here. People say “personalize”, but personalized is what all of those CRM’s sell where you put in their first name and the name of the last blog post. Don’t think of it as personalizing it, because that’s way too easy to automate. Be thoughtful. Actually be thoughtful. That’s the litmus test is what’s going to make this person open this email and say, “They actually thought about this.” Copy and pasting – like you said – is nothing.

Andy: Not at all. I get tons of emails like that where it’s just the standard format where I immediately go into my “ask” and send over my URLs. But going back to what I was asking before, is this the end of the process or is there a next step where you take your content?

Len: Great question. So, putting content out there and getting distribution for it is really good. It’s obviously a critical step. But what do you do with all that traffic? If you do the job well, then you’re going start seeing some traffic and probably in the beginning you’ll start seeing a good amount of social traffic. That’s usually a pretty good indicator that you’ve done a pretty good job and months down the line that will turn into organic traffic for you.

But if you’re seeing that traffic and you’re not doing anything with that traffic like nudging them or encouraging them pretty strongly to subscribe to your email list, then that traffic is gone. And a lot of companies make this mistake where they wrote a blog post and the call to action on their blog is exclusively, “buy our product”. And that’s fine, you can test it. But here’s the reality, most people aren’t ready to buy your product.

The very first time they hit your blog, most people aren’t ready to pull out their credit card and do business with you. But if that’s the only option you’re offering is binary, either I’m going to pay you money or I’m not. And most people are just not going to pay you money yet the very first time they meet you. Would you just whip out your credit card and pay some guy on the street that just answered a question for you? You wouldn’t. It’s like if you stop someone to ask for directions, are you going to whip out your credit card at the end and ask if they’re selling anything.

It doesn’t work that way. So businesses who just try to sell in every piece of content and in every single impression, they leave a massive opportunity on the table. So what I recommend doing is making it really easy not just to buy from you, but let’s say they don’t want to buy from you but you don’t want them to leave, there’s a middle ground. They can just give you their email address and sign up for your email list and get more of the value they’ve already got.

This is actually something that we’ve had a lot of fun testing over the years. There’s a lot of different ways to do this and there are great tools out there to help you collect and capture email addresses. You can A/B test different calls to action, different sign up forms, different types of sign up boxes. But one of the things we’ve had the most fun testing is seeing what incentives actually get people to give you their email address and to sign up.

At first we just played with different sign up forms, and people would sign up and we’d convert around 1%-2%, depending on the post. And we were plugging along with that for quite some time. And then we saw a lot of marketers do this thing that they call “content upgrades” or “lead magnets”, where you’ll see, “Give me your email address and I’ll send you this ebook.” So we tried that and we put out an ebook. It wasn’t very resource intensive to put together, it was essentially a compilation of a bunch of posts that a lot of people hadn’t seen yet. But it was valuable to people and we put it out and started offering it in all of our posts. Those conversations jumped from about 1.5%-5% overnight.

So we thought, people really like free stuff. How can we leverage that knowledge and get even more people to sign up by making our free stuff even better. How do we make our free stuff even more interesting to people? So that’s when we got into actually targeted content upgrades for the different pieces of content that we put out. So we did this test and we put out a post called, “17 Email Scripts To Grow Your Business”. It was a bunch of different email scripts that people could use for sales and hiring and recruiting and management, all sorts of different things. The scripts were great and they were the ones that had worked for us, so we made an ebook out of them so people could get use out of them. But they were all screenshots. They were screenshots of how the scripts looked in Gmail. So you couldn’t actually copy and paste.

So it was valuable, but it wasn’t the complete extent of the value we could have provided. And what we did was we had a pop-up over that that said, “grab all of these emails in an easy copy and paste format, just give us your email address.” So that conversion box, from the first hour that we put it up, started converting about 22% and it hasn’t dropped since.   

Andy: For real?

Len: Yes, for real. So 22% of the people who read that post give us their email address. That is a crazy number.

Andy: That’s huge.

Len: So I would just encourage people to think about when you incentivize people to give you their email address, how can you make that incentive so sweet and so tied to what they’re already getting value out of, that they can’t help but sign up it’s so totally irresistible.

Andy: I think what you just said, that it’s tied to what they’re reading about is why having the call to action of “sign up for our free trial” doesn’t always work. Most of the time they’re not reading anything that directly translates to your product. If it’s an article that actually makes sense where your product solves a problem that you’re trying to read about, sure. But in an unrelated article no one is going to do that. You need to give them something that’s actually related to what they’re doing right now.

Len: 100%. That’s a super smart point and it’s especially true with a blog like ours. And I suspect with a lot of the blogs the people were listening to, we have a customer service software product, one of our blogs is just about startup growth. So if somebody is reading about how to manage a remote team or how to raise money for venture capitalists, and you get a popup that’s a customer service offer, you’ll just make them confused and turned off. It just doesn’t work

Andy: You gave us so many good – I was going to say “tactics” – but these aren’t tactics, this is more of a marketing philosophy of how to think from the ground up and build a content marketing approach that really does work. And I’m excited to get all this put up together in the show notes, but to wrap things up I just want to go over a few quick questions. Are you good?

Len: Yeah, let’s do it.

Andy: The first one is, what do you spend too much time on?

Len: That’s a great question.

Andy: And this can be in business, in your personal life, just anything. what do you think when you look back at the end of the day you shouldn’t have spent so much time doing this?

Len: Ok, I spend way too much time on subreddit's and online communities that I have no business in. And the reason why is, as a marketer I find the psychology of how people interact with one another incredibly fascinating. Because that to us is like, if you can master that, you can do anything.

So I’ll find myself on the relationships subreddit. I’m happily married and don’t need to be on the subreddit. But I’ll just go and be a fly on the wall and just read for hours all of their relationship problems and advice people have. And I just find it super interesting how humans interact and work. So I could probably spend a little bit less time there.  

Andy: But at the end of the day like you said, that’s kind of just how marketing works, is understanding that psychology. So hopefully at least some of that time is well used.

Len: The other way that marketing works is through marketing, so if I’m cutting into that time, then that’s not helping.

Andy: But so going with that, what do you think you don’t spend enough time doing? If you got an extra hour a day to be more productive, what would that hour be spent doing?

Len: That’s another good question. If I had another hour, I would spend it finding amazing writers and amazing content marketers to grow our team and help with a lot of the output. We have really ambitious goals, especially for 2017, we’re trying to churn out a lot of content and I’m spending a lot of time on that. I’ve spent a ton of time building the team, and I wish I had another hour in my day to find amazing people to help us out. So if you’re listening…

Andy: The last question really does with that. What are your goals for the next year, what are those big, hairy goals for 2017 that you want to accomplish?

Len: That’s a great question. So we just recently launched a content marketing course, it’s closed now. It was a six week paid course and we had over 100 people sign up to take it with us, and I’m super excited to help people actually succeed in content marketing. So that’s a big goal for me next year is to have 100 people who took this course and actually built profitable content marketing machines from it.

And then other than that, just continue to seize the momentum and keep going. We’re probably going to have to – when we hit the $100k MRR milestone a couple of years ago, our original blog was Groove’s Journey to $100k in MMR, we had to change the whole title of our blog to $500k in MMR. And we’re almost there. So one of our big goals next year is too early in the year, change that goal again and start making progress towards it.

Andy: Awesome. Well I’m excited to see that change. Can you say what you’re hoping to change the goal to?

Len: We’re not actually sure yet. We’re not 100% sure yet because we want it to be achievable, but you want it to be a stretch.

Andy: You want to push yourself a little bit.

Len: You gotta stretch. I mean, one of the best pieces of advice on goal setting that we've gotten is from our growth coach, Kris Kaplan, who said, “Set a goal and a deadline so that you think that on the very last day that you’ve given yourself, you haven’t been at that goal for 2 weeks and you’re about 2 weeks from hitting that goal, but you’re not just sliding into homeplate.”

Andy: That’s really good advice. So Len, I just want to say thanks so much for taking the time to chat with us today. And if listeners want to learn more about the experiments that you guys are running, if they want to see this content marketing machine in action, where should they go?  

Len: They can go to groovehq.com/blog. We’ve got a blog on our content marketing growth journey, we’ve got a blog that will help you get better at customer service, and we've got a whole 300-400 pieces of content that you can learn from all the different tests and things that we’ve done over the last few years.

Andy: Awesome. I’ll make sure to get everything linked up in the show notes, and I just wanted to say thanks again for coming on the show today, I really appreciate it.  

Len: Of course. Thanks so much for having me Andy, I really appreciate it.