Siimon Sander, serial entrepreneur and founder of Oscar Hamilton and PodcastWise, recounts the early days and the new frontier of podcasting, why not to be so patient with things (give it 6 weeks), how to have a vision but keep it flexible, and talks about making friends with ChatGPT, how entrepreneurship = delegation, 3 essential steps for staffing and workflow, the problem with making yourself a hero as the leader, and why you want to work ON your business, not IN your business.

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Welcome to the Action Catalyst.

Today we're talking to Simon Sanders.

Simon runs a portfolio of profitable internet businesses, including about hire Oscar Hamilton, podcast wise and why Charlie originally from Estonia.

Simon also invests in early stage tech companies on the side, and has hosted his own podcast entrepreneur, decoded, which was number one in several countries.

Upon its debut.

Simon, welcome.

You've called Estonia home your whole life.

Is that.

. Siimon Sander: Yeah, I was born in, uh, tall Estonia.

It's a country of 1.4, 1.4 million people.

And yeah, I was born there, but after high school I ended up getting a ride in, you know, American College.

And I've been kind of going between us and Estonia for the past, you know, decade now.

But I still love going back, you know, once a year.

I usually go back, see friends and family, but I don't have too many connections, uh, back there

anymore.

What's your number one secret for dealing with the time?

You know, , I think body takes one hour per, um, day, you know, adjust in time zones.

So, you know, central time zone and Estonia time zone is eight hours, uh, eight hours different.

So usually, you know, eight to 10 days just giving your body a bit of time and, you know, not rushing it, but also, uh, building a company that is able to, you know, operate without you and where you don't have to be, you know, meetings at, you know, specific times or, you know, waking up at odd hours.

I think that has been a.

So 1.4 million people in Estonia came to the US for a university.

Were you always inspired to get into entrepreneurship?

Yeah.

Yeah.

I got into college.

Somehow I got in, so I went to this college called St.

Olive College, uh, in Minnesota.

Uh, it's a rather small school of, you know, 3000 people.

And I quickly realized I'm surrounded by high performers and you know, I was this high school kid who.

It wasn't necessarily a great student, but somehow I got into this latter fancy American school and you know, when you're surrounded by high performance, whether it's university or you know, a company either you know, you sink or swim.

And I kind of decided, you know, I'm, I'm gonna give this a shot and you know, do my best.

You know, somehow I managed, but academics never really interest me as much.

So my sophomore year I kind of decided to take a leap and start my podcast.

And needless to say, you can probably hear my odd accent, six, seven years ago it was even.

So you can imagine it wasn't the best podcast to start with, but it was an interesting era of podcasting because back then it wasn't as mainstream and you know, cool and sexy as it is today.

But cool thing about podcasting back then was you could get almost anybody to be a guest on your show.

So, you know, I was able to interview some of my, you know, Back then heroes, you know, mark Manson, the self-help writer who, you know, became a New York Times bestseller and you know, all these other guys that, and also women that I was, you know, never able to connect with back then.

And I ended up stuck sticking with it for 200 episodes.

And I think that's sort of the Eastern European mindset of, you know, just put the blinders on and hopefully it sticks or hopefully it.

and then I think I became a bit more self-aware and I kind of realized, you know, for one, I don't really enjoy doing this, and for two, I'm not very good at it.

After 200 episodes, I kind of decided, let's, you know, let's end this and let's do something else.

Throughout these 200 interviews, I was, you know, became friends with, you know, a dozen of guests and some of them, you know, wanted, don't you start a podcast?

With my kind of technical background and expertise, I was like, Hey, you know, why don't I produce and you know, do the technical stuff for you.

And I got my, you know, first clients as a, you know, sole entrepreneur and I was sophomore in college and that was kind of my leap into entrepreneurship.

Wow.

So you started your own podcast.

It was easy enough to actually get famous,

successful people.

Yeah, like really famous ones.

It was pretty crazy.

Who were some

of the early customers?

So obviously when you're sort of starting off on your own, you're not really resonating with big companies.

You know, fortune 500, you know, enterprise clients.

So typically you end up working with small businesses, so entrepreneurs, coaches, consultants, you know, authors, basically individual.

Folks who are kind of trying to build a dent, uh, in the, in, in the universe.

So my first client was by, by the name of Andy Simon.

And, uh, she is a corporate anthropologist and, uh, you know, she's been our client for almost six years or something.

And it's been, it's been insane because, uh, people become your friends.

It's sort of really cool to see, you know, people succeed in the long term when you.

When you first start off, you kind of realize, hey, maybe basically she told me, Hey, I wanted to start a podcast.

I might do it.

You know, 10, 20 episodes and now she's been running it for six years.

So it's, it's really cool to see that.

Do

you feel like you ever took lessons from these interviews in general that helped you apply them to building the companies that you've built?

That's an interesting question because I've been a big nerd when it comes to learning about, you know, leadership management for my whole life.

And it's so hard to kinda be self-aware about these things.

Like where did I pick up a specific piece of knowledge?

Was it from a book or was it from, you know, a conversation that we were having?

But I think the biggest thing I took away from, uh, you know, running this podcast of 200 episodes and then, you know, sorry, my own company on the side, which.

I don't think people should, should be as patient as they are.

I think entrepreneurship and business today reifies, you know, be patient, put out content for 10, 15 years and you know, eventually success will happen.

And I strongly used to believe that, you know, when I was younger.

But I think running experiments with your personal life, but with also business, you know, give yourself, let's say six weeks.

Your all, and if something doesn't work, you know, adjust the course and do something else.

I see a lot of young entrepreneurs, and myself included when I was younger, you know, spending so much time on these, you know, site projects and, you know, businesses that obviously weren't working.

You know, I didn't have to do 200 episodes to realize that this wasn't working.

And today, you know, we, we produce and work with, you know, hundreds and hundreds of clients, including Fortune 500.

We got, you know, Robby Markets, we got international monetary funds, some of the, you know, biggest companies in the.

Tens of millions of dollars or in market cap.

And I kind of realized that just run an experiment for six weeks.

If it doesn't work, move on to something else.

And, you know, set yourself a goal.

Do you wanna build a huge company or are you comfortable with, you know, having a sort of a lifestyle business?

Um, and that's kind of based on talking with a lot of just, you know, on friendly note with a lot of successful founders of this, you know, big companies.

Yeah, we, um, had a conversation recently with Chip Gaines and I asked Chip, you know, when you were building, did you imagine you would have this huge television show and it was gonna take him?

He was flipping houses and working on houses and his vision was mostly that Fixer Upper came in outta left field and they, they grabbed that.

Yeah.

So my question for you is, in a different way, it sounds similar to me.

Obviously you didn't have this huge vision your freshman year of college, you're gonna build this podcasting.

When did you start to develop a vision for what this could become?

I think it made such a great point.

You know, you kind of have to still have to put in the reps instead of, you know, doing 10,000 reps, you can maybe do a hundred or 200 and then just adjust the course.

But when, when it comes to, you know, having a vision, I've, I've never really had a specific vision for the podcasting business.

It was always, I need to pay my bills.

Um, my rent was, you know, 500 bucks a month after college.

So that was kinda my baseline.

I need to make 500 bucks and, you know, have some money to eat and go to coffee shops to drink some coffee.

So I never had that great vision and I think a lot of entrepreneurs do on the side.

I've kind of always had the vision of I wanna, you know, one day run a public company and be a c e o of that.

And that's sort of been with me ever since I was, you know, 15, 16 years old.

Hmm.

Um, but when it comes to kind of the macro level, there was never an aspir.

To run a specific revenue number or specific, uh, number of, you know, clients for Oscar Hamilton.

That being said, today, how we run things is very different.

You know, every quarter we set up specific, you know, objectives, key results for each employee, making sure they, you know, hit everything.

But that's very different than how it used to be when I, it was just me.

Yeah,

there's a good point in that because some people that I've spoken to, they have such blinders on with their vision that they miss opportunities that could come up in other conversations.

They're so focused on one thing, how do you gauge when a project is?

Yeah.

Still in alignment with what you're doing.

Yeah, I just love building site projects.

I think entrepreneurs tend to do that and it's very hard for most people, uh, to work on something for, you know, 10, 15, 20 years.

Cause, you know, you don't get those initial document hits anymore when you wake up in the morning.

It's kind of, everything is predictable.

You know, when I open up my Slack, when I open up my email, I know exactly what's gonna happen there.

Questions and the meetings I have with my team members.

So you start a site project on the site that kind of makes you a bit more excited to wake up in the morning.

And it sounds very depressing, but I think it's gonna be release and more positive way to cope with running the long-term business.

I usually come up with an idea when I'm, you know, just in a shower or, you know, taking my dog out.

And typically what I do is I find a general manager to run this business.

I find somebody, you know, scrappy, sort of young, usually, you know, early twenties.

Uh, it can be, you know, in us, outside of us, and basically they're higher.

Number one, I'll give them sort of direction where I want this idea to go.

And I'll give you a, you know, concrete example of that.

Uh, so, you know, chat, G B T is kind of exploding all, all, all over the place.

And if you haven't heard of chat, G b T, it's basically this AI tool.

Uh, with endless possibilities that Sam Altman built and, or, I mean, I guess he's the c e o with a huge team.

I'm seeing this huge opportunity here right now because it's early days of ai, especially, you know, you're able to ask this tool a question, for example, like, write me an article on whatever, and it's gonna actually give a pretty great output.

You know, this is interesting.

This is sort of like when Web 2.0 was, you know, getting popular.

Now, you know, with Crypto 3.0, there was like a couple years of.

Excitement and a lot of opportunity.

So I was like, Hey, I should, you know, do something.

So I came up with a blog idea, I called it Why charlie.com, and we are going to basically answer all questions, uh, with starting with why, why is sky blue?

Why should I wear shoes?

Why should I go outside when it's cold?

And these are the questions that are get answered, you know, couple hundred times a day, uh, or, or a month I guess.

And, uh, we also put together a couple people who sort of edit these questions because the AI is not perfect.

. So it's gonna give us an output and then editors will go through the answers, make it better, add some references.

And this is sort of a side project that I was able to take off over the weekend.

I hired general manager and general manager, hired editors, writers, and then general manager reports back to me.

And the max amount of time I have to spend on this, you know, per week is probably like two to five minutes.

and I'm gonna give it, typically what I do is a give projects around six months.

Cause with seo, with all of that stuff, six weeks is too, too little.

So six weeks, six months to, you know, see if it, you know, breaks even.

And hopefully, you know, becomes a profitable business that runs its

own.

Hmm.

So you're, uh, a big part of your formula is also finding the right talent though, to support that initiative.

Yeah, I think hiring talent is probably the number one skill of entrepreneurship.

I mean, entrepreneurship at the end of the day is delegation.

Nothing really more than that.

And finding very good people who can, you know, who can do work better than you in specific areas in, in the business.

And, uh, finding these people is really hard.

Uh, so I'll give you an example.

The chief of staff, uh, basical.

Who was secondhand to me when it comes to, you know, running the company.

She runs all the operations at Oscar Hamilton.

And I was just kind of overwhelmed with everything that I was doing and I decided I need to hire somebody to help me.

So I put together, you know, a job post chief of staff salary rather high, you know, top 10% I think.

And I interviewed maybe 70, 80 people.

And, uh, it was really hard to find somebody.

So I.

The biggest thing is make sure you have enough qualified leads in the pipeline.

So if you're interviewing for any position, most entrepreneurs, you know, interview 5, 10, 15 people and then they pick the best possible one.

Never do that.

Have at least, you know, 70, 80.

You know, some people say, you know, 150 plus candidates in pipeline.

Second thing, you know, don't rush it.

Uh, take some time.

If you honestly feel like the person isn't a player, don't hire them.

It's going to cost you in the long.

. So ideally you wanna have every single person on your team who's an A player, meaning that they'll take responsibility for their work.

You can tell them, accomplish this goal, and they're going to, going to go out there and, you know, accomplish this.

Most people are unable to do that, and so if you're giving out tasks for your employees instead of goals, you probably have higher wrong people.

A hundred percent.

You've obviously made some great hires.

What do you feel for you has been some of the biggest pivot points personally?

I mean, even this year you dealt with some really big health things, right?

Yeah.

So I run my business very differently than I think most internet CEOs.

Um, because I prioritize my personal time, my time with my partner, my family.

I like going to, you know, brunch in the mornings.

I like to take long, long walks with my dog.

I like reading, you know, I like going to gym.

So, , all of this stuff takes up a lot of time.

And if I was working eight to 10 hours or 12 to 14, like most, most of the CEOs, I wouldn't have time, you know, for myself.

So I kind of decided two or three years ago when I was just overworked and you know, this has to stop.

I very strategically thought about all functions that a company had.

So let's say you run at a profitable company and you're working eight to 10 hours and you wanna stop typical entrepreneur, you know, does that, so write out all the functions that your company has from accounting.

Collecting invoices to sending out sales letters, to checking in with your team, one-on-one meetings, and then make a note, uh, to everything that you actually wanna do.

What are your strengths?

What are your weaknesses?

And everything that isn't your strength and you don't enjoy doing, you need to delegate with somebody else on your team.

So you have this huge list of unit tasks.

And typically a typical company, a small, small business has.

40 to hundred functions like that.

At Oscar Hamilton, we have around like 70 functions that get executed, uh, each day.

And for each function, you need to find a person who's going to be directly responsible for that function to make sure it, uh, gets done.

You don't wanna have two people to be in charge of a function.

You wanna have one individual responsible, so if something falls true, you know who to, you know who's in charge of that.

Mm-hmm.

. You also wanna have a backup person.

And cross-train them.

So in case first person gets sick, leaves the company, there's a replacement to go right away.

So for example, if you have somebody on your team doing sales calls, they get sick, there's a second person you know, ready to take over.

The third part of the puzzle is have processes and SOPs and how to guides.

Every time anybody on your team does a task.

Second time, they are required to write it down in a written or a video format.

So for example, if I am going to collect invoices the first time, the second time, I am required to write it down so I don't have to do it again.

And that's sort of a common practice.

So once you have all these functions, you know, written out, you'll only end up with five or six things that you actually really enjoy doing.

For me personally, it's um, doing one-on-ones with my.

Hiring, firing and setting the strategy.

That's the only thing that I do when it comes to, you know, sales, when it comes to accounting, when it comes to management, when it comes to sort of the micro level that happens on a day-to-day company, you can outsource or delegate 99% of that.

And entrepreneurs often feel that they need to do it all, but in most of the time they don't.

And they not, they're not very good at it.

So being self-aware that, hey, give yourself a good space and hire.

Create those, uh, create those task lists, give out the tasks, and keep really tight eye on processes.

Uh, and you know, all of a sudden you have all this time in your hands that, and you end up working, you know, hour or two.

So, Simon, I'm gonna, I'm gonna play a devil's advocate with you, not because I disagree, cuz I 110% agree, but I know what everybody, uh, is thinking in their head is an objection to this.

And they always say, oh, Simon, but, but for me, you know, this is this task only I can do it so well.

Other people can't do it nearly as well as me.

And if I do it, they screw it up, you know?

And, and this happens, right?

You hire someone, they drop the ball.

Yeah.

And then the normal, uh, average entrepreneur, business owner wants to grab that responsibility back because they saw what happened when they delegate it.

Yeah.

It is so uncomfortable in the beginning to get this process started.

Cause I remember exactly even, you know, delegating my email box, it sounds pretty absurd, but I had this fear in my head, you know, what if somebody.

Sends out an email on my behalf and, uh, messes something up.

Yeah.

Or, you know, there's a salesperson who does a sales call and make us look, makes us look bad.

What you wanna do is, number one, you know, hire great people, number two.

, give them a trial.

You don't need to hire them full-time.

Give them one week trial and see how they do.

And for example, number three, don't give them all access.

Like on day one.

For example, with email, have them go through your email and great drafts and if they, you know, if they mess up, edit a draft and make sure you know next time you.

Change, uh, change the body of the email a bit when it's same, same thing with sales calls.

Instead of having them do 200 sales calls a month, have them, you know, start with one and see how they do.

And even if you don't trust, if you don't trust them to do one sales call, have them do like a, like a loom or, you know, one way video interview with themselves where they have pitching a, a potential client.

So it doesn't mean that you have to give out all responsibility at once, a hundred percent.

And I think that would be a bit foolish anyway.

Very slowly adjust and if you feel like person is performing, give them more responsibility.

Start off very slow.

You know, give them, you know, 10% of what you're doing.

When it comes to the question of, Hey, me personally, I can do this best.

If it's actually true, good for you.

And you can, you know, and if you actually enjoy it, make sure you can keep going and doing it.

But entrepreneurs tend to have a lot of biases and they think they can do everything really well.

And based on my experiences is not true at all.

And I'll give you an example.

, in the early days, I used to do sales phone calls and I thought, I, I'm this friendly guy, you know, I'm, I'm really good at it.

And when I started listening to the sales calls that I did, I quickly realized, Hey, I'm pretty horrible at it.

And having a salesperson who's actually trained and knows what they're doing, it's, it's a game changer.

And the moment you make that switch in their head and give it, and you give out responsibility, number one, your company will grow.

You'll have more free time and.

You have to ask yourself, like, are you fine for your companies today?

Or do you wanna, you know, have more free time and grow your revenue as well?

And if you don't, that's completely fine.

And most people, most entrepreneur entrepreneurs end up working to death for the rest of their days because they don't wanna make that switch of, you know, hiring people and giving out, uh, tasks.

It's pretty crazy.

Yeah.

Uh, you, you, you nailed it.

And then, you know, my other line of work is doing consulting and coaching, and the things you're bringing up are things that we see are very common, as you know, and it's what holds them back.

It becomes their ceiling for time.

Couple of things that I, I really wanted to ask.

One was, you have this ability, just like you're doing on this podcast, you have this ability to make it sound.

It's so simple and so easy to build all these businesses, you know?

And if we went back in time to 18 year old, you versus who you've become through this process today, you know, it, it probably sound a little bit different, but, but let us let, let the listeners in a little bit, like what have been some of the biggest walls that you've personally hit?

Yeah, I think the biggest thing for me has been the concept of heroing.

And the idea is basically when employees are having problems, challenges, there's client, you know, clients are not happy, instead of letting employees fix the problem, CEO or me jumps in and, you know, tries to fix the situation.

Yes, this is very common and I've done that so many times, um, because for various different reasons.

Um, , I think I like having full control of my company, of my business, and I tend to fall back to old patterns.

So I constantly have to remind myself and to have that written at top of my notion on my do-do list every day.

Be a c e O.

Work on your business, not in your business.

So whenever I have an idea, let's say, you know, make the landing page better.

Because I'm a, you know, I'm a, I, I bootstrapped all of my businesses.

It's very easy for me to, you know, go to Photoshop, you know, start playing around with it, spend the next two hours, you know, coming up with a cool landing page image and then realize, oh, you know, it's 2:00 PM and I've, that's all I've accomplished today, and I have this huge team.

And like, is this time well spent?

So two things.

Let your employees make mistakes.

Don't jump in and give them guidance.

Make sure they ask questions.

A good question to ask your employees is if they're stuck, what you intend to do, instead of telling them, do this through that.

So it gives them, you know, responsibility and, uh, sort of ownership over their, uh, tasks.

And second is, you know, if you wanna be a c e O, uh, it's, you know, you not need to act like one.

Cuz I don't think I acted like one for a very long time.

Uh, Make sure you actually spend your time wisely and uh, you.

, I used to track my times and I, my, my goal was to work, you know, eight hours a day.

That was sort of my threshold every single day.

And thinking back, I kind of realized how absurd it is.

You know, eight hours of work doesn't, you know, mean anything.

If the output is the same.

If I can accomplish in that in 30 minutes, so for years, I was religiously, you know, I need to get eight hours in.

Like no matter what, if it was, you know, Saturday, Sunday, any day.

And instead of, you know, having a specific threshold and or of work worked hours, make sure you're making progress where you want to go.

I think that's wonderful wisdom for, for many people, uh, heroing.

It, it feels good nature.

Do you wanna help the person?

You wanna save the business.

And so you jump in to help, but you're stealing a lesson to develop your next level of leaders.

And that's part of scalability too, right?

Yeah.

Well, a coup couple of lightning round, and these are just quick questions, but really great for our listeners.

If you were just looking at your phone, thinking of the last app that you're really excited about, what, what would that

be?

Yeah.

Notion.

Notion for sure.

Yeah.

We run everything in, not all our processes, SOPs, my own to-do list, you know?

Yeah.

If not went down, uh, I had no idea.

I have no idea what I do.

Okay.

Awesome.

Book that you've listened to or read recently that was, that was influential in helping.

Yeah,

this is available for free on, uh, in Google Docs.

It's by Matt Mockery and it's called the Mockery Method.

It's basically principles of great leadership management.

And I'll probably reread the thing like 25 times over the last, you know, three years goes over all the great management lessons from top tech companies, uh, from the world.

And, uh, Matt is just, you know, a fantastic guy and, you know, he made it available for free.

I think you can get it from Amazon as well, but the Google Docs version is more updated so highly re.

. Adam Outland: Yeah, that's a great resource.

And then because you've been in the game of interviewing for 200 episodes, I feel like this is an interesting question for you.

Who's a person you've always wanted to meet but never have?

Yeah, I, I met all my heroes.

I don't, I don't have one.

Not everybody gets to say that.

I think it's partly because I grew up in Estonia and I always looked into, you know, the Es Estonia entrepreneurship ecosystem.

I think, you know, you know in us we have these, uh, CEOs who are sort of treated as celebr.

In stone, it's very different.

Uh, you know, if you're, uh, if your net worth is thousand, millions, or you know, very, very rich, you go to the same coffee shops as you know everybody else and you're not created any differently.

So, you know, uh, you get to meet all these people very easily.

It's very different than it what's happening in the us.

Uh, so.

I don't know.

I, I don't have any specific person that I would, uh, like to meet.

I know it's a boring answer.

I'm sorry.

No, it's okay.

I think it's, it's amazing that you've had the opportunity to meet many of those people already, which says something.

I guess the last thing, and this may be a little generic, but we'd love to hear different answers.

What's your morning routine?

What's your morning routine during, in the work

week?

Oh, you're gonna hate me for this again.

This is so boring.

This is so boring.

My day is so random.

You know, I work a couple hours a day, so I typically, I go to bed around, you know, midnight, maybe 1:00 AM.

Last night I was on my laptop until 6:00 AM you know, just playing around.

So typically I wake up, you know, 10:00 AM sometimes 9:00 AM Uh, I make my coffee.

I go on a long walk with my dog, typically for like an.

and, uh, I don't take any meetings before, typically before 1:00 PM This was, you know, kind of the first in five years, which has been interesting.

And I try to get all the important stuff out of the way Before lunch, I do lunch in around 2:00 PM uh, so the morning routine literally is coffee and, uh, going out to walk with my dog.

I used to do, you know, morning pages and meditation and sort of all of that.

And it became, I felt like I was just not enjoying it as much.

Maybe I need to get back to it, but I feel like I'm getting a lot done these days.

You know, morning is my prime time.

Mm-hmm.

and I just really enjoy getting my coffee and, you know, starting, starting working after I got a, get a bit of fresh air.

So, yeah, I don't have any, any monitor routine at this.

Appreciate the

honesty.

And I honestly, we, I think we asked the question because, uh, I think it's healthy to understand that you don't have to be a morning warrior that starts at 4:30 AM to have built successful things and, and maintain growing them.

Right.

There's a lot of different ways to find that success.

I think in the, the underpinning of, of a lot of this conversation has been, you've been a student of the game and learning a lot of these principles through practice.

I feel like there's a lot of golden nuggets in what you've shared, but I really appreciate your time today and, and thanks, uh, from our audience too, for being willing to share the lessons before your 1:00 PM traditional meeting time.

Thank you.