{PODCAST} In-Ear Insights: Lessons Learned From 3 Years in Business

{PODCAST} In-Ear Insights: Lessons Learned From 3 Years in Business

In this episode, Katie and Chris discuss the lessons learned after three years of being in business. What things went well? What things surprised us? What would we do differently? What’s on the horizon? For entrepreneurs and the curious, lots of takeaways about building a company from scratch.


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{PODCAST} In-Ear Insights: Lessons Learned From 3 Years in Business

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Machine-Generated Transcript

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Christopher Penn 0:02
This is In-Ear Insights, the Trust Insights podcast.

In this week’s in In-Ear Insights, we’re going to go ahead and save you the pain of any singing.

But we just celebrated of the public announcement of TrustInsights.ai.

The company was founded in December 2017.

But we did not launch until we formally wrapped up our employment with our former employer.

So March 19 2018.

at IBM think that was the year we launched the company.

So here we are, three years later, later.

Katie? What? Looking back, what what have you learned? What are the things that maybe do differently? It’s been, it’s been a long and interesting road, including things like, you know, a global pandemic.

Katie Robbert 0:55
Yeah, I can’t believe it’s already been three years, it’s, you know, on the very first day, I remember sitting down in my house in my home office thinking, Oh, crap, now, what do I do? Because it was literally day one.

And I was just like, I, I don’t know where to start, I don’t know where to begin.

And then sort of fast forward Three years later, it’s a no brainer, like, I have plenty of stuff to do.

There’s emails, there’s, like, you know, a whole bunch of stuff.

But, you know, in terms of what I would do differently, I think that, you know, one of the things that I don’t know, if a lot of people know is that we actually came up with this idea and made the decisions to launch the business pretty quickly.

This wasn’t something that was like years and years of writing out business plans and thinking through things like you and I, Chris had made the decision had had a conversation and made the decision in the course of about 48 hours.

Um, because we just sort of knew it was the right, yeah, we knew it was the right thing to do.

And so we were on a trip to California, and during that trip is one, we figured out that this is the thing that we wanted to do.

And so that was maybe two months before we filed any sort of incorporation papers.

See, I’m okay.

You know, so what I would do differently is, you know, definitely not, you know, slow down, but I think I would really try to do a little bit more research around the right way to file the incorporation paperwork, because we had originally filed as a different Corporation structure than we are now.

So it’s like, it’s those things like, you know, the state that you file in the structure that you file for, it’s those things that I think I would definitely maybe take a harder look at.

And it’s not that you can’t walk back from it.

But it’s just sort of a pain to try to do that, when you’ve already like that you have the stamp of approval, it’s not easy to go through all of that paperwork.

It’s very time consuming, and very mind numbing.

And so once you get through it, the thought that you have to go through it, again, is very daunting.

Unknown Speaker 3:16

And also expensive to,

Katie Robbert 3:19
yes, it is also expensive.

And that’s the other thing is so, you know, I think that in terms of what I would do differently, like any startup, you know, we kind of we didn’t have our own money to sink into it.

So we were going to look for investors.

And that was one of the reasons why we incorporated the way that we did.

And looking back, you know, I kind of wish we’d had a little bit more faith in ourselves, that we didn’t need those investors.

Because ultimately, we didn’t find investors, we made the decision to completely build the business without that backing without that safety net.

And it’s been great.

We don’t have a bunch of faceless people that we have to answer to in terms of every decision that we make.

And, you know, we did run into some issues in trying to find investors and the type of feedback and advice that they tried to give us just did not jive with who we are and what we wanted to do.

It didn’t feel good at all.

And it actually made us panic a little bit.

And so just looking back, that would be the big thing that I would probably do differently is just not not worry about that aspect of it and just have a little more faith in you know, ourselves and what it is that we’re capable of.

What about you, Chris?

Christopher Penn 4:41
You know, I think I wouldn’t have changed a whole lot.


One of the things that we discovered very early on, as we start to interact more people who would you know, potential partners and things was that, you know, once we got to look behind the curtain as it were under the hood, we found a That what people and businesses things portray to the outside world is not even remotely close to the reality.

Once you get under the hood you like, wow, it’s entirely powered by hamsters.

There’s no magic here.

It’s it’s, it’s just, you know, hamsters on wheels.

And I think that’s, that also speaks to what you were saying about having more faith in ourselves, when when we looked under the hood of organizations that from the outside looked like they had it all together, they had that that professional shine, they, they looked expensive, you know, you go into, like, ah, and then knowing that, and then looking at, you know, what we had to offer even back in the day, and now going, Okay, we don’t look as expensive.

But what’s under the hood is actually functional.

Like, there’s one of the things that I’ve constantly been surprised at is that, when you look under the hood, particularly in anybody who says they’re doing things like AI, for example, you go, but you’re not doing what you say you do.

Right, as some guy towards things I definitely would not change would be, you know, we at least we do what we say we do, you actually have the the machinery that is promised, but looking at the people that we interact with him, well known members of our community and things, and going behind the scenes going, huh, there isn’t as much here as I thought there was.

So doing things differently would be, again, putting more faith in ourselves saying, you know what, it’s good to have friends, it’s good to have partners, you may not necessarily be able to rely on them as much as you think.

And they may not be as capable, as you think that they are from, from outside appearances only.

It’s kinda like what people say about, you know, social media in general, right, you know, just be like, what’s on someone’s Instagram is the highlight reel of their lives, it’s not the day to day.

And, you know, we found that very quickly, in the first couple of visits, like, wow, we, the highlight reel is really is just the highlights, and there’s a whole lot of stuff that you don’t see.

Katie Robbert 7:06
And I think that’s a really good way to frame it, because that’s exactly what social media is, it’s the perception that people want you to have of them of their companies.

You know, there are obviously people out there who share like, you know, the, in the weeds, you know, sort of, like less pretty parts of their lives.

But for the most part, people are sharing, you know, the filtered images with the carefully crafted captions.

And, you know, that’s, I think you’re absolutely right, that’s a lot of what we were deceived as the wrong word, but sort of duped by in terms of what we thought we were walking into with, you know, clients and partners.

And, you know, when you, when you really start to dig in, you’re like, oh, you’re just like us, nobody has any idea what they’re doing.

And they’re figuring out, literally, in the minute.

You know, that said, I think in terms of something that I’ve learned, is, I will say, and this is a little bit of like, you know, tooting my own horn, but like, I feel like I talked to the CEO role, kind of like a duck to water.

I’ve always enjoyed being in charge.

I mean, this is, you know, you can ask anyone in my life, this is something I was born with, I was born needing to be in charge.

But in terms of, you know, sort of, like the operations and the planning, and the forward thinking, you know, it’s, it’s funny, I often hear like, Oh, you know, they have to be like, these big thought leaders and strategic thinkers, and you know, the idea guy, and when you really break it down to what it is what that means, it’s somebody who has an idea, and then can put an executable plan behind it, and then execute that plan.

And that is the thing that I can do, and therefore I’m like, oh, okay, I can do that.

And I went into the role being very intimidated thinking, I don’t have enough experience.

I’m not old enough, you know, I’m a female, so it’s going to be really difficult.

And none of those things have really been true.

You know, it’s literally just Okay.

Here’s where you are today.

Here’s where you want to be tomorrow.

How do you get from today to tomorrow? Or how do you get from today to next month? Or how do you get from today to next year? What’s the plan? How are you going to get there? How are you going to measure it? How are you going to make it happen? What do you need? And that to me is like okay, that’s literally what I do, I can do that.

So I think it’s what I’ve learned is, it’s not that the job isn’t hard.

It’s very hard.

It’s very difficult.

Some days are better than others, but to not be afraid of, you know, chasing after the thing that you really want.

What about you, Chris? What is some stuff that you’ve learned?

Christopher Penn 9:55
Well, I just want to comment today the role is called Chief Executive Officer right.

Execute things about Chief idea officers not chief Big Mouth officer, right? It’s It is literally get the thing done at the company level and stuff.

So you know to that, to that end, that’s exactly what you do is you get the thing done.

You’re right that that sort of the outside world has sort of layered on these, these additional things that a CEOs theory should be known for.

But at the end of the day, you got to get the thing done, you got to make the company profitable.

You got to make sure it workers stay employed, the taxes get paid.

And yes, there’s operations officers and things add a lot of bigger companies, but the reality is always still rolls back up to the corner office.

So yeah, in terms of what I’ve learned, it’s been a fun and interesting trip.

Because in every other role that I’ve had, prior to this one, I kept getting, you know, moved higher and higher up the management ladder, which but I ended up doing less and less actual work.

You know, I remember that first week, like we were talking about, you know, I looked at the calendar two weeks prior, when we were at our old job and the 35 of the 40 hours a week were meetings, like no actual workers games, just meeting after meeting.

And then two weeks later, it’s like, oh, look, there’s large swaths of time.

And it’s gotten me back into the operational side of things, I’m just doing the thing.

And it’s been an amazing trip from that perspective.

Because getting back in the weeds, getting, you know, doing the thing, writing the code and stuff has been a delight to be able to sit down and actually play with stuff and make things.

When we came into the company, we had some ideas and things that we kind of brought with us.

Certainly a lot of knowledge that came with us.

But in those first few months, and continuing through to today, we’re actually building the things as we think they should be not as you know, somebody who’s trying to put us as an add on to it another service.

But it’s like no, this is actually think like, just this morning, I’m working on building some new code to build attribution models for Google Analytics for one because it’s going to be the thing.

And whether we like it or not, we’ve got got to work that no one else is saying, oh, it must do this, it must do this, it must do this.

Because this client wants it this way.

There’s no it’s it’s our professional judgment and experience to say, this is what we know is in the box.

This is what we can build from it, and it’s gonna iterate, it’s gonna change, it’s gonna evolve over time.

But just having that freedom to say, yeah, I’m going to do it my way.

Is, is really, very uplifting.

Katie Robbert 12:36
Well, and I, you know, I want to sort of mentioned, so you had said, you know, in previous jobs, like 35, of the 40 hours a week were stuck in meetings, I think that there is this misunderstanding, of, you know, importance.

And so I definitely bought into the idea when I was much earlier on in my career that the more meetings I had, the more important I must be.

And so I think that that’s a tough mentality to shake, if that’s what you’ve been taught, of, if you’re sitting in meetings all day, people must value you and value your opinion.

And that might be true.

But a lot of times, it’s not, if you look around it, like how productive the actual meetings are.

And if you walk away with next steps and things to do, and you know, if those things are happening or not, or if it’s just regurgitation of the same conversation over and over again.

And I definitely have an had that like panic moment of, Oh, my God, my calendar is completely free for today.

Nobody wants to talk to me, I must not be doing it right.

And now I’m like, whoo, my cow we just created, I don’t have to talk to anybody.

That doesn’t mean that I’m not communicating with people, it doesn’t mean that things aren’t moving forward.

I love having less meetings.


It’s fantastic to your point, you can actually get back into the Getting Things Done versus just sitting, you know, in meetings, like, you know, we sat in a meeting last week with one of our clients, and it wasn’t our meeting, it wasn’t my place to jump in and be like, and do what I do, which is takeover all the time.

It just wasn’t the time and place for that.

And, you know, we left the meeting, and you and I said, Well, so what’s next? And there was no next step.

There was no follow up set, there was no action item, there were no assignments.

And to me, that’s just a waste of time.

Like why bother? And so it’s it’s nice to be able to set that precedent for the company, and really challenge the people who are trying to, you know, spend time with you and take your time to say, What value do we both get out of this conversation and be able to say that to people be like, Is there an agenda? What do we want to accomplish and if there isn’t, okay, we’re not having this conversation and it sounds A little harsh.

But we’re now in positions where we can protect our time and be more productive and not just spend it, you know, on the phone and on meetings for no real good reason.

I love it.

Christopher Penn 15:12

So in terms of where the company is going, where do you feel as the CEO as as, as the grand vision

Katie Robbert 15:23
as the grand visionary thinker,

Christopher Penn 15:25
exactly, where do you see things going in terms of the company, as a as a micro project, and then sort of the macro, the bigger picture?

Katie Robbert 15:36
You know, so the micro, I think that we’re definitely going to keep, we’re just going to keep doing what we’re doing, we’re going to continue to try to add value, and solve problems for marketing teams that are stuck in some way, maybe they’ve gotten in their own way, and maybe they don’t have enough resources, maybe they don’t have enough experience.

And so really, the value that we bring to the table is, you know, we plug into an existing team, and support them and help them move forward to the point where they can then start making decisions with their own data.

And so I see that just continuing on in different iterations, whether it’s, you know, a new attribution model for Google Analytics, four versus Google Analytics, three, you know, really keying into what is the pain point that you’re having? What problem Can’t you solve, that Trust Insights can come in and help you solve? And so I see that continuing in terms of sort of the bigger picture.

You know, I think that we’re going to continue to focus in on really good smart partnerships, because we are a small business, and we can’t do it all.

But when you find really good partners that complement your skills, then you grow together.

So I think that that’s definitely something that we’re going to continue to do.

You know, personally, and I’ve said this a couple of times, in different conversations, I would like to keep us as small as possible as long as possible.

I don’t know how realistic that is.

But there is something nice about not having, you know, a dozen people running around doing a whole bunch of different things and trying to wrangle the circus, having a smaller team allows you to be more agile.

And so I would like to stay agile for as long as possible.

You know, I think that we’re going to continue to hit bigger stages, I think that we are going to continue to, you know, do more interesting and innovative and cutting edge things with artificial intelligence and respect to the marketing space, because it is still a very new thing.

People talk about it a lot.

There’s a lot of conversation around AI, but there’s not a lot of doing.

There’s not a lot of actual results and output.

So I think that, you know, Trust Insights is at the forefront of that.

And again, sort of as we have the right partners, they can help us get that message out.

Christopher Penn 18:00
I was just recalling the quote from Dan Ariely about about AI and big data and stuff.

The mildly inappropriate was like AI is like teenage sex, everyone’s talking about it, nobody actually has any idea what they’re doing.

So there you go, macro wise,

Katie Robbert 18:20
holy, unnecessary.

Christopher Penn 18:22
It’s in the third edition of the book isn’t the second edition to macro wise, when we look at the last year, especially governments around the world, but the United States government in particular, were based, printed, fortunately, in Dallas, like, brand new out of thin air, fortunately, extra dollars, and that cash is sloshing around in the financial system, it’s sloshing around to the banks and institutions is one of the reasons why cryptocurrencies has done so well this past year.

And as things wind down, thankfully, with the pandemic, and things reopen, we should be looking at like 1945 1946 right, what happened after the Great War and you suddenly saw this massive boom, as people got back to normal life, I think that we’re going to see that I hope that we’re going to see that in the world, you know, in the second half of 2021, and then 2022.

And I know for our company we want obviously would want to play our role in a making sure the companies make good decisions as you open up and be helping them to retain the things that they’ve learned I mean a lot of companies for good or ill had to do a digital transformation in 2020 right they had no choice like Yes, you were staying at home and you know, you’re gonna live on zoom.

And certainly there’s there’s a balance to be had but a lot of companies go look at look back at this and go well, we were forced to become digital, you know, even just like the mom and pop, you know, sub shop or like we got a handle online ordering because Ain’t nobody coming into In the store to eat anything.

And I think that is where there’s a lot of opportunity, not just for Trust Insights, but for every company to say, Okay, well, what are we going to keep? What stuff? You know, do we learn? Like, yeah, actually 70% of your workforce can work remotely, maybe not all the time.

But certainly, you know, thinking back to the way off spaces handled, you don’t need 100 seats with 100 bucks in it every single day, right, you can maybe have 40.

And then people can stay home when they don’t need to come in.

And then on those days, when they do have to have the eight hours of marathon meetings in the conference room, they can come in and use the conference rooms.

So I think we’ll still see a lot of the digital transformation that happened continue on, possibly accelerating spaces.

And again, I think it’s one of those things where, hopefully, we can continue to prove to to our customers and our prospective customers that yes, we have some value out there too.

Because I’m very optimistic about the year ahead.

Katie Robbert 21:01
And I, I am as well.

And I think, you know, with that optimism also comes, at least from me gratitude.

And so, you know, one of the really great things that has happened as a side effect of building our own company is having better work, non work life balance.

And so you know, I’m home every day, you know, pandemic or not, we started as a remote company.

And so I’m home every day, I have one of my dogs behind me on screen, the other one was on screen and then left the room, but I get to be home with my family every single day.

And if I need to take, you know, an hour or two or even a day, nobody’s gonna yell at me about it, like things are still gonna get done.

We have a lot of trust amongst our team and our clients that we’re not going to start dropping the ball on anything that if I’m suddenly dark for a couple of hours, unless I’ve said something’s really wrong, you guys like okay, bye, see you later.

And it’s been a really nice, you know, change from the grind of working, you know, other places, not just any one place in particular.

But in other jobs where that nine to five is drilled in, it has to work this way, you have to be available for these exact eight hours, no more or no less, rather.

And I’m really hopeful that with the pandemic, that companies realize that the nine to five is an unsustainable model, that you know, as people are home with their families have lives, you know, they need to go to doctor’s appointments, they need to run errands, and not everything can be done on a weekend, because sometimes, myself included, your spouse works through a weekend.

And so something that you need them for, can only happen during a week day.

And so it’s I’m grateful that Trust Insights has allowed me that kind of flexibility to have whatever schedule I need to have in order to get things done, build the business, but also have a life.

And I feel like for you, Chris, you know, I’ve seen that change in you as well, where I see that you have a lot more work life balance.

Since we’ve built the company, even though it’s our company, we work really hard.

I’ve seen you actually have more of a comfort level, stepping back and stepping away and saying, Okay, I’m not I’m not online during these hours anymore.

Christopher Penn 23:33

And, you know, as looking down the road, it will be very interesting to see, because one of the things that is true of all startups is that the DNA of the startup really is set in those first, first five employees, right, those first five employees really set the DNA for the kind of company it becomes.

And when you look at the company, you know, decades or even hundreds of years later, like a company like IBM, you can see that the culture that Thomas Watson created in those first few formative years has persisted.

And for all that’s good and bad about that, you know, those those, everything gets magnified.

And you know what the lesson for anybody thinking about starting their own companies, you have to spend a lot of time thinking about the culture and the tone, you’re going to set what is and is not okay.

You know, one of the things that we did very early on, if we wrote down our values, the things that here’s all the stuff that we hated in the past companies we worked for, and things and then the What do we want those things to be going forward.

And with any kind of company that you’re that you’re building, particularly start bringing on employees or even contractors, you know, if you’re going to be working with a network of freelancers, you will still have a culture that is set by those initial plank holders and it’s very difficult to change.

Once the organization is gone.

It’s very, very difficult.

When you look at a lot of the things that are happening now hearing people being held accountable for inappropriate behavior in the workplace.

You don’t have to look for look at the first five employees and how they behaved in the workplace, and you’ll get a sense of how deep the problem goes.

So if the if there’s a takeaway from our experiences, you know, as a company, as people it’s know in advance what kind of company you want to work in want to build.

Katie Robbert 25:17
And I think, I think we’ve done that, Chris, I think that we have absolutely been building the kind of company that we’ve always wanted to work at that has, you know, it allows for that flexibility, but it also allows for that space to innovate and test and fail and learn and grow.

And that’s not something that you can get everywhere.

And it took us a while to feel comfortable setting aside that time, that wasn’t necessarily client work.

It’s like, Okay, let’s go test and build something, and maybe it’ll never see the light of day.

But that’s okay.

And I think that that’s one of the things that we really wanted to be able to do.

And so here we are doing it.

Christopher Penn 25:57

But even other base things that, again, are not necessarily things that you think about me starting company, but again, it gets imprinted into the way the company functions.

You know, we’re, we’re equally split, female founder and a minority founder, right, we didn’t set out to do that, necessarily, it’s just, that’s just the way it worked out.

You and I share exactly the same rate of pay, you know, so we have there is no parity gap between genders, and there never will be in the company, you know, people will be paid entirely on merit alone.

But those things that again, if you don’t, if you start with something that’s off kilter, it just gets worse as time goes on.

If you start with something really solid, it gets more solid as time goes on, because it becomes part of the foundation for what comes later.

Katie Robbert 26:46
I wholeheartedly agree.

And I think actually, that’s a really important point that perhaps people aren’t aware of is that Chris, you and I are 5050 all the way to the end, you know, there is no difference in what either of us are worth what either of us, you know, if down the line we decide to sell, we will get the exact same share of things.

Because even though we do different jobs, we both equally bring value.

And we’ve you know, we came to the conclusion early on that neither of us could have done this without the other person because of those complementary skills.

And I think that that was one of those really, you know, unique things to our professional relationship is that we recognized early on that our skills were so complimentary, let’s go do something with this.

And they continue to be complimentary, even almost to a comedic point where like, we’ll get on the phone with clients.

So by God’s the Kristen, Katie show, but it’s all out of mutual respect.

And at no point has there been like, why did I start the company with this person like that thought has never crossed either of our minds that I know of.

You know, and so that’s a really unique and special thing that you know, if you can find that person that you trust, and that you can work with, and that you can, you know, respectfully push back on.

And they can do the same for you.

Like, hold on to that and think about what you can do with that relationship and how that can help you and the other person grow professionally.

Maybe it’s not starting a company, maybe it’s just partnering on like, side projects, or working together on something.

But, you know, if you find something like that, then definitely take advantage of it and do something with it.

Christopher Penn 28:33

I think that’s a great final lesson.

If you’ve got questions about this, or anything that we’ve talked about on the show, why not stop over at our free slack group go to Trust insights.ai slash analytics for marketers, or 1600 other marketers chatting about all things marketing and analytics and such and there and wherever it is that you’re watching or listening to the show.

If you have a preferred channel, you want to get it on go to Trust insights.ai slash ti podcast, you can find most things the other place we really aren’t is Tiktok.

next time, take care want help solving your company’s data analytics and digital marketing problems.

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