Welcome to the latest episode of Entrepreneur’s Enigma! In this conversation, Seth sits down with returning guest Brendan Hufford, a former teacher turned entrepreneur with a wealth of experience in the world of marketing and entrepreneurship. They discuss Brendan’s journey from teaching to working in the SaaS world, and his current projects, including a newsletter aimed at marketing executives, a community for in-house software marketers, and helping SaaS companies scale their revenue. Brendan shares his insights on marketing, the importance of transparent content, and the value of reducing suffering through service. This episode is packed with wisdom, laughter, and valuable takeaways for all entrepreneurs. Tune in to hear the full conversation!

Key Moments

[03:22] Struggle to find marketing help, communities lacking.

[08:07] Need ample time to decompress before work.

[10:58] Influential solopreneur markets through strategic networking.

[12:38] LinkedIn lacks authentic storytelling and success is gradual.

[16:29] Advising on hiring, organization, creativity, accountability, marketing.

Find Brendan Online

https://www.linkedin.com/in/brendanhufford/

https://growthsprints.co/

https://allinhouse.co/

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Follow Seth Online:

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Transcript provided by CastMagic.io

Seth [00:00:00]:
Entrepreneur’s Enigma is a podcast for the ups and downs of entrepreneurship to the wins and the fails that we all face being entrepreneurs, how we learn from adversity. Every week I talk to a different entrepreneur with a story to tell. I’m Seth Goldstein. Come with me on the journey. This is Entrepreneurs Enigma. Let’s get started. Hey, everybody. Welcome to another edition of the Entrepreneur’s Enigma podcast, episode 213.

Seth [00:00:36]:
The reason I mentioned it, the date the date the the the the issue number, I can’t speak today. The episode number is because Brendan was my 4th guest originally on Entrepreneur’s Enigma way back when, and now he’s 213. So this is awesome, and a lot has changed. I mean, he’s done a lot. He’s and he before the podcast, he says he does one new project project a year. Thing is he might do one project a year, but he doesn’t get rid of another project, though.

Brendan [00:01:07]:
Correct.

Seth [00:01:08]:
He just adds on 1 a year, and this is like, this guy has more projects than I do. And and people who know me know that I always have something up my sleeve. Brendan is a former teacher, a recovering teacher, if you don’t, you know, haven’t been following along since. Yeah. Recovering teacher. I mean, you did it. You I’m sure you enjoy moments. But, like, you know, being a teacher is one of those thankless jobs where it’s like you put your all into it, and it’s never good enough.

Seth [00:01:36]:
Either the kids criticize you, the parents criticize you, the administration criticizes you. It’s just it’s tough. So but he survived that, and then he has been in the SaaS world since then. He’s been in house, and he’s been out of house, I guess, entrepreneurial. You know, he’s he’s in the side hustle. He’s done the full hustle. He’s done this full hustle and a side hustle for his full hustle. Like so, Brendon, how’s it going, buddy? How are you doing?

Brendan [00:02:04]:
I’m great, man. I’m excited to chat again. It’ll be good to catch up. It’s been it’s been definitely

Seth [00:02:10]:
At least a year.

Brendan [00:02:11]:
Since the first time we did this. It’s

Seth [00:02:14]:
Oh, that’s been, like, 2 years. Yeah.

Brendan [00:02:16]:
Yeah. I I had to look it up, man. August 2021 was definitely Yeah.

Seth [00:02:22]:
I think it was

Brendan [00:02:22]:
definitely a very different time in my life. It was

Seth [00:02:25]:
in your life and in the world.

Brendan [00:02:28]:
Absolutely.

Seth [00:02:30]:
Definitely. So fill me in. What’s changed?

Brendan [00:02:35]:
So I’m trying to remember exactly. So I think you

Seth [00:02:38]:
were active I think you were at ActiveCampaign. You were at a full time hustle and, like, 16 side hustles.

Brendan [00:02:44]:
Yeah. I so I was at ActiveCampaign, but I was still doing, a lot of stuff on the side. Right? Yes. So I have this problem where I see things that I want to exist in the world, and I usually complain about them once or twice, and then I go make them. That hasn’t transcended into, like, software or anything yet, but it usually transcends into platforms and media and community and things like that. So I had I went in house in the end of 2020. We first kinda recorded and chatted in 2021. And what I’d done when I went in town, I’d always been agency side previously.

Brendan [00:03:22]:
And when I went in house, I was like, I’m looking This is hard. This is a different kind of hard than agency. Where can I find some help on this? And it did not exist. Like, all the marketing slacks, I paid a $150 a month for Pavilion. I was trying to pay every community I could get into to just find this stuff out, and it did not exist. There was nothing that existed because it Just what you need. Yeah. Marketing communities mostly suck, especially the ones you pay for.

Seth [00:03:53]:
Yeah. I noticed that.

Brendan [00:03:55]:
Sound like they’re better if you pay for them, but they’re not. It’s it’s actually worse. I know this sounds crazy. People are like, well, they’re more curated. People are paying to be here. It’s not gonna spam me. It’s actually the opposite. People feel entitled.

Brendan [00:04:07]:
Like, I’m paying for this. I deserve to spam, you know, to do a LinkedIn every week of, like, listen to my podcast. Here’s me on LinkedIn or just like, and I hate that. And I was just like, this is just a bunch of marketers promoting themselves to other marketers. Where is the place that you go to figure out how to navigate this, like, faded pirate treasure map that is, you know, corporate bureaucracy?

Seth [00:04:32]:
Oh, sorry. It’s it’s something. Yeah.

Brendan [00:04:34]:
And I realized pretty quick that, like, I wasn’t great at that. I’m I I really struggle with, let’s have 30 meetings to have 30 more meetings about maybe launching a page 2 years from now. Like, that just how slow that move

Seth [00:04:50]:
is really concentrated. Yeah. There’s a reason why with my with my agency, we don’t touch enterprise For that reason, it’s just too much bureaucracy, too much, like how many people do I have to hand hold to get something done? It’s just not worth it.

Brendan [00:05:03]:
I had a big company tell me one time they couldn’t hire me because I had less than 10 employees. What? Which is just, like, one of the most insane like, do you imagine why that rule was created for them internally? Like, what happened in your company where you’re like, we only work with contractors that have more than 10 employees? Like, I it did stuff like that. You know? Like, I I agree. The same. Like,

Seth [00:05:24]:
in big companies

Brendan [00:05:25]:
big companies and small companies, there’s a reason I say on the Growth Sprints website that I am perfectly a fit to help companies scale from 10 to a 100,000,000 in revenue.

Seth [00:05:35]:
Mhmm. What that what that

Brendan [00:05:36]:
really means between me and you and everybody listening and watching is, a, can you get the work done? Do you have enough resources to actually do the thing? And then second, are you gonna be awful to work with? Because really small really small software companies

Seth [00:05:52]:
Yeah.

Brendan [00:05:52]:
In my experience, my red flag is, like, if I get on and I’m talking to a founder and they’re, like, really excited, like, I kinda know it’s gonna go bad because they don’t have anybody in marketing, and they think that I’m gonna come in and work magic and that they don’t really understand marketing either. So I’m gonna make recommendations, whatever. They’re not they’re gonna be under that’s the thing I’ve heard, only from, like, the solo founders I’ve worked with.

Seth [00:06:18]:
Yes. Solo founders are tough.

Brendan [00:06:20]:
This is kind of underwhelming. And I’m like, I’m not here to impress you. I’m here to make you money. Like Yeah.

Seth [00:06:25]:
It’s a little different than yeah.

Brendan [00:06:27]:
Come up with a bunch of wacky stuff that’s like, wow. Brendan’s so cool and smart. Like, I can do that. Yeah. But most of it won’t work, but, like,

Seth [00:06:34]:
what am

Brendan [00:06:34]:
I hearing? You know what I mean? It, like, misaligns instead of the same thing again on the big company side. Right? If I gotta have 40 people on the call to present Ugh.

Seth [00:06:41]:
This is awesome.

Brendan [00:06:42]:
Content strategy, like, we got a problem. So you know what, man?

Seth [00:06:46]:
Sweet spot. It’s the sweet spot. Like, big or small, nor midsized, but not too big. Yeah.

Brendan [00:06:53]:
Yeah. Not in that I think that the the reason that that’s been going well Yeah. Was like I had kinda said, I think it was early. We’re coming up in April. I had to put it on the calendar because, honestly, I forgot, like, when when I quit my job. You would have thought it would have been, like, a bigger deal, but, like, I didn’t it it’s the same as when I went from teaching to working at an agency. I literally the school year ended on a Friday, and Monday, I was in the office.

Seth [00:07:19]:
You didn’t make any time. Yeah.

Brendan [00:07:20]:
And it’s the same thing with doing my own thing full time. I just the next week started, and I just had less meetings than I had before.

Seth [00:07:29]:
Oh, that sounds wonderful.

Brendan [00:07:30]:
And it wasn’t and it wasn’t, like, any big deal because everything had already been running. There’s this wonderful book by Sean McCabe called Overlap. Yeah. Sure. Talks about, like, overlapping your thing you’re doing now with your next thing, and you just keep, like, stacking, but they always should overlap. And I was like, that’s the best analogy. You know?

Seth [00:07:51]:
We’re gonna take a quick break, hear from our sponsors, and get right back to the show. I love that. Yeah. It’s so true because, you know, having a gap in stuff mean, it doesn’t always look good in your resume. But not just that. Having a gap, you get stale. Even if it’s a week, it’s like sometimes you need a week. Let’s say maybe to be honest.

Seth [00:08:07]:
Sometimes you need to decompress. But taking more than a week to get into your next gig is it’s tough. You have to kinda at that point, you’re you’re almost in vacation mode at that moment. Because you isn’t there there’s a favorite book or somewhere that said that, like, the 1st week on vacation, you’re just decompressing. You’re not in vacation mode till you’re in the 2nd week. Like, you have to take 2 week vacations just to get relaxed. And so it’s it’s wild, man. So you’re doing you have a you have a newsletter which everyone should sign up called Growing Up.

Seth [00:08:39]:
I love it. I just signed it today, and you know you had it. So I was like, oh, sign up for this. Absolutely. You are the founder community lead for all in, which is all in house dot co, which is is was is is the community you were talking about. Right? Is it’s the one where it’s, like, in house, helping people actually get what they need from a community.

Brendan [00:08:57]:
Yeah. And it’s it’s free. I keep it small on purpose. Yeah. And it’s just for in house software marketers.

Seth [00:09:05]:
Very focused. Exactly what’s needed.

Brendan [00:09:08]:
Yep.

Seth [00:09:09]:
That’s brilliant. And then, of course, you have grossprints, which is kind of helping it was what we were talking about, helping SaaS companies go from 10,000,000 to a 100,000,000 ARR ARR. That’s a hard to say one. So that’s you have a framework and all that stuff. So, I mean, you’ve done this, and you can you kinda tell your school teacher. Like, everyone says you never journals never left me. Teaching elephant never left you.

Brendan [00:09:32]:
100%. I think you can have still the art of mine.

Seth [00:09:35]:
Your education.

Brendan [00:09:37]:
I just wanna share everything I know. Like, I don’t Yeah. Grant, I you know, I got a I made a post on LinkedIn over the weekend, that, got a lot of attention because it was me airing out some frustration with people who don’t tell you the whole truth. People who will say, oh, I made a $1,000,000 last year, or I made $700 in the last 6 months by my course. You know, it’s always, like, you know, just typical Pitching.

Seth [00:10:06]:
Yeah.

Brendan [00:10:06]:
Online marketing. Right? Like, I’m gonna make I’m gonna make you feel less than. I’m gonna make a hole in you so you feel like you can fill it with my course or my coaching or whatever. Yeah.

Seth [00:10:15]:
But the

Brendan [00:10:15]:
problem is I know all those guys that post that stuff, and they never explain to you. I know behind the scenes of a bunch of their businesses, and they never tell you the whole thing.

Seth [00:10:25]:
They’re already a 10 year overnight success.

Brendan [00:10:28]:
Or just like, you know, there’s a guy who’s always talking about how he makes $1,000,000 a year as a one person design agency. And he sells a course on how to do that, obviously. Funny enough, the course has also sold $1,000,000. Weird. Mhmm. And now it’s but what he doesn’t tell you is he’s he’s been hospitalized twice for stress. Like, he still hasn’t figured out how to not almost die from doing the thing that he’s selling you. Right?

Seth [00:10:55]:
Yeah. Or the guy who’s going operation is insane.

Brendan [00:10:58]:
Yeah. Or, like, the the $4,000,000 solopreneur, who’s gonna teach you how to be a solopreneur, but his main revenue stream is teaching you how to write tweets in LinkedIn posts. And that’s a that’s a different but what he doesn’t a, that’s a it is what it is. Yeah. And his stuff is good. I bought it. But what he doesn’t tell you is that the reason his stuff gets a lot of reach is because of all the back channel networking he does, where he hooks up with 30 other creators, and they all They they

Seth [00:11:26]:
they have their little, share stuff. Yeah. The share service.

Brendan [00:11:29]:
Or it’s Yeah. You know, I’m on yep. I’m on Linked I’m big on Linkedin. I wanna grow on Twitter. So what he did was he found a bunch of people who are big on Twitter that weren’t on LinkedIn, and he’s like, let’s let’s work together. Yeah. And how

Seth [00:11:41]:
I had

Brendan [00:11:42]:
how I went ROI happens

Seth [00:11:43]:
from that, and that’s just why I’m also

Brendan [00:11:45]:
sell in a course. Right? Like, I hey. I would I would actually I would actually pay more. I’d pay $10 for that course if you were like, hey. Here’s how to build, like, strategic partnerships. Yeah. Absolutely. But they don’t it doesn’t the problem is it doesn’t sell as clean as, like, let me teach you how to tweet.

Brendan [00:12:02]:
Right?

Seth [00:12:02]:
Exactly.

Brendan [00:12:03]:
So stuff like that tweet. I just want people to teach the whole thing. Like, keep the levers and share the levers that actually work.

Seth [00:12:12]:
But not everyone’s an educator, dude. That’s the thing. Not everyone’s an educator and has a mindset of education. There there are business people. I’m not saying you’re not a business person, but they’re not dealing with background in education where you tell the whole story. And then if you wanna know more, they buy your course because they already have some they already have actual content they can just go wrong with. Great. But then but people buy from people they know, like, and trust too.

Brendan [00:12:37]:
Absolutely.

Seth [00:12:38]:
That’s a big thing, I think, that is missing on LinkedIn. It’s like, a, we’re we’re just doing you know, we’re posting them for the sake of posting for the algorithm, And, b, you know, we’re not telling the whole story, which is very frustrating. And it makes everyone feel like, well, why am I not doing that? Well, and that’s it goes back to the whole thing over the 10 year overnight success. A lot of these people say, like, I’m making a $1,000,000 this year. How long have you been in your business for? Or how long have you been doing this for in general? You may have changed your name of your company a bunch of times. Oh, it’s been 10 years? Oh, that makes more sense because 1st year, everyone’s scrambling. I mean, if you I mean, you might hit that one big ticket item that might get you with 200 grand. Great.

Seth [00:13:19]:
Mazel Tov. You know? Great. Good for you. But, like

Brendan [00:13:22]:
Yeah.

Seth [00:13:23]:
Can you have people that, like Yeah.

Brendan [00:13:25]:
They don’t explain. They’re like, oh, here’s how I made, you know, 700 grand as a consultant, and you’re like, 500 of that came from a contract with a guy that you’ve known for 15 years and your kids go to school together. Or, like, they’re not explaining, like, how they get like, what was the because you can’t sell that. And anytime somebody’s selling if they’re like, I’m making an insane amount of money doing this, here it is for you too.

Seth [00:13:54]:
It’s never that replicable.

Brendan [00:13:56]:
I especially if it’s a service Mhmm. Where you’re now creating competitors, that’s a question mark for me. Or it’s just also a lame flex. Like, all it does is make people feel bad. Nobody reads how much money you make and is like, wow. I feel better now that I’ve read that. Like, it it really does just make people feel bad because the majority if you’re flexing how much money you make, the majority of people are making less. And, dude, I went through that for so long when I was a teacher, and I was making $25 a year.

Brendan [00:14:27]:
And it felt like everybody was winning faster than me and making more than me, and it was so hard to keep going. Mhmm. I constantly ask myself, like,

Seth [00:14:39]:
when I’m creating same thing.

Brendan [00:14:40]:
Yeah. Yeah. Any content, any anything I’m doing, does this I this sounds really wild, but, like, I really do believe, like, the our purpose as humans Mhmm. Right, is to reduce like, life is suffering, and if life is suffering, my job is to reduce the suffering of everybody else as much as possible. As of service. And that’s very existential. But the way that looks in marketing is like

Seth [00:15:06]:
have this real behind just to kinda make sense. Or Aristotle.

Brendan [00:15:10]:
No. Yes. It’s the same.

Seth [00:15:11]:
Dude, he’s actually old dude with a good beard and good hair. So there you go.

Brendan [00:15:15]:
He’s he’s bigger than like, I’m 61 and, like, 260. I’m a big dude. And, like, he’s bigger than me. I didn’t know the the statue was that big. Like like, if I scoot back, you’re like

Seth [00:15:25]:
Oh my gosh. It’s huge.

Brendan [00:15:27]:
Way bigger.

Seth [00:15:29]:
Oh my god.

Brendan [00:15:30]:
So, like because

Seth [00:15:31]:
that this is if for those who are not watching the video on YouTube, YouTube, go look at your YouTube just for that one clip because that that it adds a big statue.

Brendan [00:15:40]:
We’ll, we’ll make a we’ll make a special clip of it. We’ll make it a short. Absolutely. The, but my point is, like, I that sort of thing like, so much of how I go to market

Seth [00:15:52]:
Yeah.

Brendan [00:15:52]:
Is, like, what can I make that answers the questions nobody’s answering right now? Like, the Growing Up newsletter, I I work with so many CMOs and VPs of marketing, and I’m like, nobody is there’s nobody out there create like, there’s all these, like, you know, interview podcasts with CMOs and things like that. Yeah. And I love that, and they usually talk about career path, which is important. But nobody talks about, like, the stuff that actually helps a CMO be successful. Right? Like, how do you the same

Seth [00:16:21]:
the same industry where they’re where the last 18 months as CMO and you’re it’s the turnover and CMOs are crazy.

Brendan [00:16:29]:
Yes. And a lot of that is, like, how do you hire? How do you organize your meetings? How do you structure your teams? Mhmm. How do you, you know, stay creative but also keep people accountable? How do you think about, you know, making bets in your marketing? Like, I wanted to pull that out of people that I admired, and it’s like that has grown a lot. Mhmm. And people are like, this is and it’s not like a general, you know, generic resonance. Right? Like, I think I have 27,000 people on my email list, but I I’m pretty sure close to 10,000 people have unsubscribed. Yeah. Right? Because they thought they were gonna get, like, tips and hacks and SEO stuff, and I’m like, no.

Brendan [00:17:06]:
No. No. Like, here’s how to actually have a successful career. And they’re like, yeah. That’s sounds hard.

Seth [00:17:11]:
Well, then then then then then then fine. You don’t want them on your list, and that’s the best way to prune your list. I mean, it’s a whole another episode. How to prune your list. Get rid of 10,000 people where it’s not painful. So

Brendan [00:17:21]:
I do that all the time. I look at the people who haven’t opened emails in the last couple months and just unsubscribe

Seth [00:17:26]:
them. Yep. Well, it’s a cost. It’s a it’s a cost. And, also, there the chance for your unsubscribes and your spam and links and all that stuff for people to put you in spam. It’s better to get rid of them before they do anything. It’s just like get rid of them. So

Brendan [00:17:40]:
Yeah. And, like, what’s the incentive here? Is it this is, again, we get back into, like, what is what are we actually doing? It would be it would look way better if I posted on LinkedIn, you know, I built my email list to 50,000 people, and a 100,000 people read my emails. Like, that looks more impressive.

Seth [00:17:57]:
How many unsubscribed?

Brendan [00:17:59]:
Yeah. And but or just like it’s a 100000 people, but it’s a 12% open rate. Right? Like, that That’s

Seth [00:18:05]:
not quite open rate, actually, come to think of it. It’s not a bad open rate. 12%.

Brendan [00:18:10]:
Yeah. Yeah. But I mean, like, I’d rather keep it smaller and have, you know, 67% of people read at least 1 email a month, which is where I’m at right now. Like, I love that. Awesome.

Seth [00:18:19]:
I wanna have my mind recently, the last 3 came out and they were like 80% open rate. And I was like, oh my god. I mean, I also I’m writing to write, and if they don’t read it, fine, whatever. You know? It’s it’s but I’m like, my openings are insane. And people are like, how are you doing? I’m like, this is very good content. And people wanna read it. And then those who don’t wanna read, unsubscribe. Good.

Seth [00:18:40]:
Mhmm. Yeah. It’s that simple. So, Brendan, where can people find where is the most best watering hole for you right now? Because you’re all over the place.

Brendan [00:18:48]:
I mean, it’s definitely LinkedIn. That’s where I share something cool every single day.

Seth [00:18:51]:
You do? It’s fantastic.

Brendan [00:18:53]:
And you already mentioned the newsletter. It’s kind of a mix between here’s my best advice, here’s the best stuff, like, from a journalism standpoint, like, doing the exploring and the interviewing and the researching Mhmm. Of how to do your job as a marketing executive. And then also a bit of, like, news and things like that. Like, here’s some stuff you might not be aware of to stay current. I think that is also super important

Seth [00:19:16]:
Yes. As

Brendan [00:19:16]:
a marketing leader. But, yeah, you can also here’s the other thing. You can also Google me. I’ll pretend it’s because I’m good at SEO. But if you Google Brendan Hufford and you just sound it out as best you can, you you You’re

Seth [00:19:27]:
not like Seth Gold’s you’re not like Seth Gold’s, and we’re just like it’s like the Smith of Jews. Like, you know, like, literally, everyone’s last name is Goldstein, and and and and add Seth in front of it. There’s a and there’s a famous Seth who is an angel investor in south in SoCal or not in SoCal, in San San Francisco. We used to always get each other’s tweets back when I was on Twitter. You know, I he was at Seth, and I was at Seth Goldstein. So I would forward him tweets if people were tweeting to me when they issued it in between to Seth. And I’m like, oh my gosh.

Brendan [00:19:56]:
Funny. I

Seth [00:19:56]:
understand that. I was you can’t tell me because of that. So

Brendan [00:20:01]:
Who is it? I always use the example of Justin Jackson, who’s a guy that I love. No chance. Like, no. There’s a there has to be so many Justin Jacksons in the world.

Seth [00:20:11]:
He’s just right after that. Yeah.

Brendan [00:20:13]:
Yeah. Yeah. But, I mean, he’s I think he’s, like there’s, like, 6 professional athletes named Justin Jackson. Like

Seth [00:20:20]:
I’m I’m on the top for Seth M. Goldstein because I use it as a journalist, But I don’t like to use my middle initial, and I’m really upset that, like, I want a second page for Seth Goldstein, but I’m like, hey. Now with the continuous scroll, it’s not that bad.

Brendan [00:20:35]:
Well, I’m better at SEO than Seth. So I’m I’m on, paid one and number one for Brendan Hufford.

Seth [00:20:41]:
Oh, god. Love it, buddy. Alright, Brendan. This has been so much fun. Let’s make sure it’s 9 or 2 years before we get you back on or at least us chatting in general because this is always a blast, buddy.

Brendan [00:20:50]:
Yeah, man. I love it.

Seth [00:20:52]:
Awesome. And guess what? We’ll see everyone next time. That was a great show. If you’re enjoying Entrepreneur’s Enigma, please view us in the podcast directory of your choice. Every review helps other podcast listeners find our show. If you’re looking for other podcasts in the marketing space, look no further than the marketing podcast network at marketing podcasts.net. Gold theme gi. I hope you have enjoyed this episode.