Simon is a career digital entrepreneur having built and sold a group of content affiliate sites in the mid 2000s before then setting up an agency group that was acquired by IPG PLC in 2016. At the time the business employed 125 people but grew quickly during earn out, becoming a business of 270+ people by the end of 2020.

That business started life as a performance and content marketing agency and Simon spent ten years as a thought leader and expert in the space – so many now look to his expertise in sales and marketing now. The business eventually became a full service digital agency.

Alongside this Simon started angel investing in 2016, realising that the early stage world was in desperate need of not just cash but people who had been there and could help guide and support founders properly. Along that journey he met three other angels with a similar world view and from it Haatch (an early stage venture investment fund) was born.

That business, alongside his consultancy Scaled has been his focus over the last 6 years and he now spends his time helping and supporting B2B businesses grow fast and with less ‘pain’ and sits on a small handful of Boards also.

Key Moments

[06:10] Scaling business is challenging due to people.

[09:22] Transitioning from business to private equity focus.

[11:13] Investing: Spotting talent, guiding, equally rewarding.

[13:22] Embrace opportunities to improve social networks.

Find Simon Online

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

scaled.co.uk

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Transcript Provided By CastMagic.io

Intro Voice Guy [00:00:14]:
You’re listening to Entrepreneur’s Enigma, a podcast about the ups and downs of the entrepreneurial journey. Every week, your host, Seth Goldstein, interviews entrepreneurs from all walks of life about their entrepreneurial journeys. From store owners to fortune 500 CEOs, we all have stories to tell. So sit back and join us for the next 20 or so minutes while we explore the entrepreneurial world.

Seth Goldstein [00:00:49]:
Hey, everyone. Welcome to another edition of the Entrepreneur’s Enigma podcast. Today, I’m here with Simon. Simon, it’s Penson. Right?

Simon Penson [00:00:57]:
It is Penson.

Seth Goldstein [00:00:58]:
I got it right the first one. I was very reluctant on it because I wanna say pension, but there’s no I. You know? I’m trying to make sure. Simon is a career entrepreneur, but he’s also a former journalist like myself, which I thought was very cool. I thought that was kinda neat that we both come out with the journalism route first, then it was like, nah. Let’s go to digital. But but the difference is Simon is now an angel investor. He has sold his company, and he’s now angel investing.

Seth Goldstein [00:01:28]:
But his his whole idea is not just to invest money. It’s also to help the the his investees, I guess, that’s the term, with advice and strategy and it’d be an an adviser as well as an investor, which I love. Because a lot of times people you can just throw money out of problem with it. It doesn’t always fix things. And I mean, you’ve been around the block a while. We’re the same age, and it’s makes sense to have an investor who gives a crap, pretty much.

Simon Penson [00:01:57]:
Just to put it bluntly. You know, you’re right. It’s not about being smarter or better. It’s just to, like, you know, having lived through those things. Right? There’s there’s super value in that, isn’t it, irrespective of who you are and what you’re doing. And, Yeah. It’s a big kind of purpose led thing of mine now to, find a few people to take a list even a little bit of that pain away, I think.

Seth Goldstein [00:02:15]:
I love it because, I mean, that’s all I do. I feel the difference between angel and VC. These angels give a crap. VCs just want to return.

Simon Penson [00:02:23]:
Yeah. I think that I mean, yeah, that’s certainly been true of the past, actually. I think Yeah.

Seth Goldstein [00:02:27]:
I think some VCs are different, but yeah.

Simon Penson [00:02:29]:
Yeah. I think that is generally, you know, like, you know, the financial investor will look at the numbers and not really care about the, you know, the story, the people behind it and the, you know, the pains that they go through. Right? And, you know, why should they, I guess, because that was their job and role. And, you know, actually, I think if you’re if you’re raising money, you you know, it should be your job to understand that and actually do a lot of DD on the people that put the money in because there’s very different types of money.

Seth Goldstein [00:02:54]:
Absolutely. But so before you went into, angel investing 2016, you were doing the digital marketing world. You’re in the marketing world. You had a agency that was I think it says here up to a 125 people, which is impressive. I mean Yeah.

Simon Penson [00:03:10]:
We got bigger in the end, but yeah. Oh, 270. Oh. Yeah. By the end. Yeah. Yeah. Because No.

Simon Penson [00:03:19]:
Yes. Well, you have to leave those things in the end because that’s that’s quite a burden to carry, isn’t it? But, yeah, we we did know. We had great

Seth Goldstein [00:03:26]:
Were they on the office? May 2020, I guess they weren’t.

Simon Penson [00:03:30]:
Yeah. Pretty COVID. So, I mean, we had more than one office by that stage. Obviously, we were UK based. We were, London Leeds and Peterborough and, yeah, lots of people.

Seth Goldstein [00:03:41]:
Wow. You see, on me, it’s me and 3 other people. I keep it small and nimble. I can’t I can’t imagine trying to manage 270 people. I mean, yeah, you had other managers managing, obviously, but still the buck stopped with you. You know? So how did let’s let’s go back to the beginning. You you you say journalism, you went into journalism, you you worked for a mag the magazines over in the UK, which we all know the magazines in the UK are better than the ones in the United States. We always look at them in the States saying, oh my god.

Seth Goldstein [00:04:12]:
Why are they so expensive? Well, because they’re such so high quality. I mean, all the web design magazines back in the day, like there was a web design magazine. It was like $20 for an issue. You didn’t get it yet. They didn’t import it, but it was such a good it was such it was I was not gonna go to Barnes and Noble and get it. I pick it up and I keep it for months and get go through it and scratch through it. Always has CD. Remember those? Had a CD of, like, you know, tidbits of this, those of that, on that kind of thing.

Seth Goldstein [00:04:38]:
That was an above board, you know, above and beyond for the magazines over there. So how did you go from digital I’m not no. From journalism to digital marketing? Like, how did that whole start? Like, how did this whole entrepreneurial journey start for you?

Simon Penson [00:04:54]:
It’s a good question. I think I think you kind of always got an in user degree, haven’t you? And I I was working in publishing. I could see that going a bit like that to print. So A

Seth Goldstein [00:05:03]:
little like that?

Simon Penson [00:05:04]:
Yeah. Audiences were migrating, weren’t they?

Seth Goldstein [00:05:07]:
Let’s be honest here. Yeah.

Simon Penson [00:05:09]:
Yeah. Exactly. And I, I’ve been building my own sites. And, you know, I think through doing that, I told myself how the Internet works a little bit because it’s sort of the late nineties, early 2000. Mhmm. And through that process, really, it kind of could see the writing on the wall print. And so, you know, eventually, they, you know, they’re sizing well enough to build me a runway to leave the corporate world behind the 10 years in the corporate. You know, built run those on their own for 12, 18 months, sold those.

Simon Penson [00:05:37]:
They gave me then the the runway to be able to build what became the agency business, if that makes sense.

Seth Goldstein [00:05:43]:
Wow. Yeah. So we it was similar trajectories in the beginning because I was doing websites on the side, you know, and then, you know, journalism burned out. So, like, this is not where I wanna be anymore when digital marketing makes logical sense. So you went into so so you did the journalism thing. You went to the digital agency. What was the best thing about running an agency versus kinda doing your own thing on the side as, like, a a hustle? We’re gonna take a quick break here from our sponsors and get right back to the show.

Simon Penson [00:06:10]:
It’s funny, isn’t it? Because it and, like, the the the answer to this, I think, is, like, juxtaposed in some respects because, you know, like, you like, in an agency by its very nature has lots of people in it. It’s not just about you, and actually, that the hardest thing often about scaling business is the people aspect. I think certain people, and I, you know, I classify myself as one of them, like, really enjoy that challenge of people and, you know, enjoy the challenge of culture and leadership and mission and all of those kind of things. And that’s the that was the difference, and that was the key driver for me. And, actually, it’s weird because when I exited, I ran away from agency a little bit. Didn’t wanna know anything about it because I was done.

Seth Goldstein [00:06:51]:
Yeah. Well, in 2020, you I mean, you got in. Wait. Wait. You got in, like, with mid 2 odds, and you ran it for what? You ran it for, like, 16, 17 years. I mean, that’s not

Seth Goldstein [00:07:02]:
a while.

Simon Penson [00:07:04]:
Yeah. It’s a while.

Seth Goldstein [00:07:05]:
You can burn out from that. You can say I’m done. Yeah.

Simon Penson [00:07:08]:
Yeah. So, you know, you do, and you you kind of but then you decompress and you miss the you understand what you’re missing, and then you end up missing it if that makes sense. And so now now that’s why I kind of lent back in, you know, through kind of advisory consultancy stuff at least because, you know, it meant that you could stay close to those sort of people and actually Mhmm. Help them through that journey a little bit, you know, and talk about mistakes

Seth Goldstein [00:07:28]:
a little bit. Yeah.

Simon Penson [00:07:29]:
Yeah. Like, I’ve done that stupid thing, and this is what happened. And so if you avoid that And

Seth Goldstein [00:07:33]:
they kind of avoid it. They kind of avoid it. They always kind of still do it themselves, though. You know? Yeah.

Simon Penson [00:07:38]:
Yeah. There is an element of that.

Seth Goldstein [00:07:40]:
Exactly. I mean, I I still dabble in journalism because I I burned out. I’m I miss it, but I miss it. I miss the whole idea of journalism writing and all that stuff. And so, like, that’s what I do. I mean, I have my newsletter. I have my podcast. This is journalism in a way, you know, kind of thing.

Seth Goldstein [00:07:54]:
You know? But I still do digital marketing as my main driver. So so how many angels I mean, how much angeling do you do? Angeling. I’m I’m calling a new term here, angeling.

Simon Penson [00:08:06]:
I know what you meant. So, like, I saw I saw I’m sort of mainly investing probably about, sort of 2015, 16, and realized through that process that, you know, to your earlier point, the most of that world was run by, you know, people that, you know, looked at spreadsheets and, you know, from from those backgrounds. And what they really needed actually was was the help to kinda grow because, actually, you throw money at a problem, and it creates a bigger problem.

Seth Goldstein [00:08:31]:
It often does. Yeah. Because they just keep spending on the problem that is they’re having. It’s like, no. No. No. No. No.

Seth Goldstein [00:08:36]:
You guys change course first, now throw money at it. That kind of thing.

Simon Penson [00:08:40]:
Yeah. And that’s exactly it. And that was my experience. And, you know, I I, you know, met met some people that sort of shared the same worldview, starting and investing together, and then sort of we sort of collectively ended up, sort of launching a sort of regulated fund that, you know, today, which is, you know, a fantastic leading UK, sort of, early stage investor. So, yeah, learned a lot through that journey as well.

Seth Goldstein [00:09:06]:
So do you only invest in UK companies, or you venture across the pond? Like, what, like, what what actually, about this. What’s your sweet spot in investing? Is it other agencies? Is it cool start ups? Is it, like, how

Simon Penson [00:09:20]:
are your

Seth Goldstein [00:09:20]:
products? I don’t know.

Simon Penson [00:09:22]:
Yeah. So I’m in that business, which isn’t actually I’ve I’ve backed off. So I’m I’m sort of no longer actively involved as of kind of this spring, but the business continues to do really well and that and it really focuses on b to b SaaS, b to b software businesses, and predominantly in the UK. It’s starting to expand into other areas. And I’ve I’m kind of spending the time that I was spending on that business now kind of focusing on sort of, like, later stage. So kind of working a bit with private equity because, you know, my passion is really, you know, going back to this kind of purpose thing of being able to really help. And so I wanted to have fewer deeper relationships, basically.

Seth Goldstein [00:09:59]:
Yeah. And concentrate more on the quality over the quantity, which makes sense. And, also, at later stage, I feel like in your early stage, you get them before they make the mistakes. Later stage, you gotta get in there and stop them for making a mistake, adjust, and sometimes it’s like turning the Titanic sometimes.

Simon Penson [00:10:16]:
Yeah. Yeah. Yeah. Iceberg. Yeah. Yeah. I’m picking it. It’s the challenge, isn’t it? But it’s, you know, like you say, you learn stuff, don’t you? And, you know, all of those kind of good things.

Simon Penson [00:10:25]:
So, yeah, just started that journey really. And, you know, now I do

Seth Goldstein [00:10:29]:
quite a bit

Simon Penson [00:10:29]:
of work with product x. It’s just sort of also to help them, you know, like, know what they’re buying and buy the right businesses.

Seth Goldstein [00:10:35]:
That’s fun. Yeah. So what is it I mean, you did corporate, you know, corporate journals, which is, I think, sometimes worse than corporate corporate. What what’s the best thing about being an entrepreneur in your mind? And then even in what best thing about being an angel investor in entrepreneurs?

Simon Penson [00:10:51]:
Yeah. I I think entrepreneurship is kind of a new, isn’t it? In some ways, I’ve, you know, I think there are times where you describe it almost as an affliction as opposed to, you know, kind of a, you know, something you have to do. And sometimes you question your sanity in doing it, but equally, it has incredible highs, doesn’t it? Yeah. It has bad lows, terrible

Seth Goldstein [00:11:06]:
The doping the dopamine rushes. It’s real. It’s real.

Simon Penson [00:11:10]:
Yeah. It really

Seth Goldstein [00:11:11]:
depression.

Simon Penson [00:11:13]:
And, yeah, and and the only investing piece, I think, you know, equally, you know, it’s very rewarding because, you know, you get the ability to you know, you can spot talent. You learn how to spot it faster and faster and more accurately, and, you know, you can help them go on that journey, can’t you? And, you know, you can help them make fewer mistakes, and, you know, there’s a lot of reward, isn’t there, in helping people get there. So they’re quite different things, but equally rewarding, I think.

Seth Goldstein [00:11:37]:
Yeah. I think it’s I think it’s, I mean, it’s it’s great. I do a lot of startup consulting. I don’t do the investing, but I come in, advise people on things and whatnot. And that, you know, because I don’t I don’t have the budget to invest per se. I sweat equity it in. I’m not gonna give you all my knowledge, but there ain’t no budget for me to give you money for this. You know? Yeah.

Seth Goldstein [00:11:55]:
I’ll give you my knowledge, which is a lot. I mean, 17 years of doing my own startup. I mean, it’s worth something, I guess. That kind of thing. But here’s the question. I mean, and this is what keeps you up at night? I mean, besides your kids.

Simon Penson [00:12:10]:
Yeah. They’re teenagers now. So that’s certainly Well,

Seth Goldstein [00:12:12]:
that that that keeps you up. I’m sure. Because that’s like like, what are they into now?

Simon Penson [00:12:16]:
Yeah. Indeed. But, I it’s a really good question now. I mean, I would have been able to answer that very easily, but over a long period of time, probably 5 years ago. Right? Because there were many things that were keeping me awake at night. Oh

Seth Goldstein [00:12:28]:
my god. Can I imagine?

Simon Penson [00:12:30]:
Now I think it’s it’s like, it’s picking the right opportunities, right, if that makes sense. And that you know? And I don’t mean as in, you know, like, from a selfish perspective, but actually making sure that you’re really because you’re a finite resource and making sure that you’re really lent in and using the, you know, the skills and experience that you have to to up to help the right people.

Seth Goldstein [00:12:50]:
Yeah. I mean, I think it’s totally true. It’s like not getting in too deep on stuff. Like, you’re not saying, oh, I can help everyone. Yeah. You can probably help a lot of other people, but picking and choosing the right ones, making sure you get the right ones. And then they say something weird, you know, like, do I pick the right one? Oh, no. I kinda think so.

Seth Goldstein [00:13:09]:
Yeah. So what is the most important thing to carry with you all the time? That’s gonna be, you know, as woo woo as you wanna get. So the most important thing you carry with you all the time.

Simon Penson [00:13:22]:
I would say is that lived experience, actually. And, you know, increasingly, an attitude that’s like, you know, say yes to every kind of opportunity to meet new person in a new place. Right? Because Yeah. I I I spent 10 years or however long it was, you know, like, head down, having to build something. And, you know, so my network was really actually poor. And so now I’m sort of, you know, carrying around this kind of, you know, yes and see where it kind of leads kind of attitude a little bit.

Seth Goldstein [00:13:50]:
Yeah.

Simon Penson [00:13:50]:
You know, I’ve really enjoyed. It’s been very liberating, actually.

Seth Goldstein [00:13:54]:
It is. It’s it’s it’s surprisingly liberating when you can kind of take a deep breath, step back, and just observe, and then say yes to the right things.

Simon Penson [00:14:05]:
And say yes to the

Seth Goldstein [00:14:06]:
wrong thing sometimes. So I mean, you know, so, you know, saying yes to the wrong thing is a fail, but nothing’s wrong with a fail. You know, a fail, you learn from your failures.

Simon Penson [00:14:14]:
You do. And think people, particularly in the UK, actually. I think the US I think you’re over in the US there. I think you are better at that. I think the UK Oh, yeah.

Seth Goldstein [00:14:21]:
We feel constantly. Our whole country feels constantly. Come on now.

Simon Penson [00:14:26]:
But yeah. But that’s what I mean. It’s good, isn’t it? Whereas, I think it’s kind of snared out a little bit here in the UK, and, you know, that is something that we should definitely get over because, you know, entrepreneurism for thrives where there’s, success and failure, doesn’t it?

Seth Goldstein [00:14:39]:
Yeah. I mean, like, most of my biggest successes came from failure. There’s there’s a quote right there, but I mean, literally, it’s like, that didn’t work. Oh, if I did x, y, z, media would work. Oh, it’s working. Yay. That kind of thing. So that’s always fun.

Seth Goldstein [00:14:57]:
So, Simon, if people wanna find out more about you, your investing, who the heck you are, why I had you on the podcast, why you’re so cool, that kind of thing, where do you hang out most online? Like, where what’s your choice order hall?

Simon Penson [00:15:11]:
Probably, well, probably LinkedIn. You know, it’s the usual, isn’t it? Now I think, you know, I used to spend a lot of time on Twitter. It was x now and, you know, gone a different way, hasn’t it? So yeah.

Seth Goldstein [00:15:21]:
Oh, it’s such a Britishism. Gone a different way. It’s so it’s such a polite British way of saying it’s it’s it’s a cluster f. Let’s be honest. It’s a cluster f right now. It’s it’s kinda I love that. It’s going a different way. It’s beautiful.

Seth Goldstein [00:15:36]:
I love it. So LinkedIn, and they can also find you it’s scaled Yes. Scaled.com.uk.

Simon Penson [00:15:42]:
Yeah. So I’m gonna scale to co dot UK. But yeah. And as I said, you know, I’m really happy for people to reach out because I was happy to have that conversation and say yes. So

Seth Goldstein [00:15:50]:
I love that, man. I love that. I’m so glad we got to chat. You know, this has been a little long time coming, so this is awesome. And we will see everyone next time. Thanks. Beautiful.

Intro Voice Guy [00:16:04]:
It That was a great show. If you’re enjoying Entrepreneur’s Enigma, please consider giving us a review in the podcast directory of your choice. Every review helps us reach new listeners. If you like Entrepreneur’s Enigma, consider the other shows on the Marketing Podcast Network at marketingpodcast.net.

Seth Goldstein [00:16:40]:
Goldstein Media hopes you have enjoyed this episode.