Ordinary People Doing Extraordinary Things Guest Spot

I was recently interviewed by Keri Roberts on the Ordinary People Doing Extraordinary Things podcast about my entrepreneurship journey over four businesses, including Day Optimizer, my current startup. Some of the topics we covered include:

  • What worked and what didn’t with my previous businesses
  • How to know when you need to take a break vs the idea is the right thing to pursue
  • How Day Optimizer arose from the ashes of my Strategic Life Tools membership site
  • What steps to take to effectively plan your day
  • What advice I give for those looking to start a business

Listen to the episode on Apple podcasts or read the transcript below. Or subscribe to Ordinary People Doing Extraordinary Things.

But if you set an end time, that’s this checkpoint, you can go, okay, Is this the most important thing to do? If so, go, keep working on it. You should be working on that. But if not, that’s a signal for you to put that aside.

Keri: It’s time to start being your extraordinary self and living a life that makes you happy. Each week you’ll hear stories of inspiration, conversations to improve your mindset, and actionable tips. You can take to live an extraordinary life because you matter. I’m Carrie Roberts and this is Ordinary People Doing Extraordinary Things. Hi podcast listeners. Today my guest is Trevor Lohrbeer. Welcome to the show, Trevor. Thank you for being here.

Trevor: Hey, thank you for having me.

Keri: You have been about 20 plus years now, where you have founded and you’ve run various internet and software startups. I’d love for you to kind of take us back from the very beginning. Were you somebody that was always excited about technology, were you somebody who was like, I want to be a creator. I want to be an entrepreneur someday. What were you kind of like as a young man?

Trevor: So I’ve always been kind of like a square peg in a world full of round holes. I didn’t really fit in. And I’ve got this kind of–you might call it a fatal flaw–which is that, I like to be in control of my own time and creativity, and I like to think outside the box. I don’t like a boss handing me a vision and telling me how to implement it. So I have always been bad at being a good employee, right? Like I mean, I can be one, but I’m not great at being one.

But people ask, what’s your superpower? My superpower is that I’m really good at taking a blank slate and creating boxes for other people to think within. I’m really good at creating frameworks and mental models that help people reason about the world and to solve problems.

So those two things have kind of conspired to make me an entrepreneur, And so throughout my career, yeah, I’ve built products and businesses that create new concepts, new ways of approaching existing problems that help people solve something they need to solve in the world.

Keri: Yeah. I agree with you. I definitely like the leeway of being able to kind of do your own thing and think outside of the box. And I think that’s definitely a telltale sign that you are an entrepreneur of some sort, if you’re kind of having those feelings or those kinds of situations happen. So when you started doing business, you’ve owned multiple businesses and we’ll get into the one you do now, but what was kind of the first business that you did? How did that kind of start and where did that idea come from?

Trevor: So years ago I lived in San Francisco, and worked at a startup in San Francisco back there. Now it’s the early days of the internet. At that point, I thought I was missing the boat. The internet was already passé. I had started doing some contract work for, uh, let me back up first.

I worked for the startup. We got acquired by a company down in Silicon Valley, so then I worked for that company, met a bunch of people and then left that to start doing some contract work. At that point in time, I had kind of gotten that bug of like, I want to start a business. This was 1998, so early days the internet was kind of like, everyone was starting internet businesses, you gotta do it. I was working with this one guy and I did a bunch of market research and I realized, I found this niche within the internet space. Back then everyone had a homepage, through Angelfire or GeoCities.

There were these web pages–easy ways to get a homepage or a website. And then there were all these add on services. There was a company that dominated that space called guestbook.com, where you could add a guest book to your website, and people would sign and say, “Hey, nice to visit your website”, blah, blah, blah. So think of it like the early days of social media before Facebook, this was your wall where – how people interacted with you.

I came up with the idea to create a multi-page kind of guest book, a slambook. So like, I don’t know if you’ve ever, like in high school, took the little notebook and you say, what’s your favorite color or who’s your favorite Backstreet boy or whatever. And they would pass it around class and people would fill it out. So, I essentially made a digital version of that, and that was my first product.

I spent the whole summer just locked in a room basically, like working on this product and then launched it cause I’d ran out of money, and had to go get a job, and did some initial marketing, but because it was such a viral product, it grew from 0 to a 100,000 users in nine months.

Keri: Oh really? What year was this?

Trevor: This was 1998-99. So now a 100,000 users is nothing, but back in, like ’99, that was a really great growth curve.

Keri: And so, I mean was it something that you did for fun or was it something that you started to monetize? I mean, what did you do with it? I mean, ’cause that’s so early 1998-99.

Trevor: Yeah, so the idea was always to monetize it in some way, and back then the idea was to use ads. I quickly realized I wasn’t the right person to do the ads, so I actually contracted out with another company to manage all the ads for me. So you know, I was generating regular revenue and all that, and then, I came up with the idea for my dotcom, and then–I guess that was a dotcom too–but I came up with my real, big dotcom. And so wound up selling that to the company that was managing my ads.

Keri: And how old were you when you did that?

Trevor: 27.

Keri: So you sell this company that you’ve built in your twenties. At 27 years old, were you feeling like, I made it, like I’m feeling good? I sold, I have money? I’m done, I can retire? Or were you like, okay I’m ready for the next thing? Or were you like, what do I do now? What was the feeling at that age?

Trevor: Well, I was already working on my next startup. So, in some sense, the previous one was this albatross hanging around my neck. I had to manage it. I had a support person who handled the support. And then there were all these headaches because it exploded in the teenage market, and teenagers are really mean to each other. And so there was all this moderation that had to happen. And so I was ready to kind of get rid of it at that point. I already had this other business I was founding with a bunch of other people, where we were out raising money, and that was going to be the real startup. So yeah, I was excited about that, and definitely I didn’t sell it for enough to retire, but it was definitely like: yeah I’m done, good, hand it off, now I get to work on the real company.

Keri: On to the next thing, right? You know, you were doing this for a little while. Was your background in being able to do the development? Are you doing the software development of these types of things? Were you more of the financial person? Were you more the person who was better at selling, or was it kind of a combination of everything?

Trevor: So, my background is definitely technical. My father gave me my first computer when I was nine, and so I learned through high school. My first job out of high school was doing development for the Navy, doing test software for GPS satellites when we were first launching those. So yeah, I came from a development background.

But my family–my father, is an entrepreneur and my mother’s an entrepreneur. They’ve always run their own businesses, so I always had that as a kind of background sort of thing. I definitely brought that in at that stage. Looking back I would say I was still probably 90% developer / 10% business person, compared to where I am today. But yeah, I could build it all out myself.

Keri: Yeah, alright. So what was this second business that you were excited about at the time?

Trevor: So the business kind of pivoted halfway through. How I founded it is this: I had been doing work for–the job that I took was doing web development and I rebuilt this person’s whole software platform, how they ran their whole business. He was like, “I really want to start a dotcom, I want to start a dotcom.”

So back in 1999, there was a group of people who put themselves up for auction on eBay; they were called “ISPTeam”. And they decide to put themselves up for auction to find a new company to work for. And I thought, wow, that’s going to be the future of HR. Like people aren’t going to go look for a job. They’re just going to auction themselves off, you know? So we actually formed a whole company around this idea to build an online auction for people, so people could auction themselves off. We raised half a million dollars worth of funding on that idea, and then we hired an HR consultant who basically explained to us everything about why that idea was wrong.

But at this point we had taken it–we had taken all the money. We had hired out people. We were going; we couldn’t quit. This was before the term pivot came about, but we pivoted…hard. We stayed within the HR market, but where they’re like, okay, what can we do? And one of these big unsolved problems in the HR space, is how to reach the passive job seeker, right? How to find the person who is open to an offer, but isn’t actually actively looking for a job. If you told them, here’s your dream job, they’ll jump on it. So we came up with this idea of, well let’s develop a site where people can network with each other, right? Upload your resume, send messages to each other, introduce each other.

Your listeners will probably recognize that today as LinkedIn–and it basically was LinkedIn, but we actually folded before LinkedIn started. So yeah, we pivoted to a social network for professionals called True Peers, and we got it up and running. And then in March 2000, the dotcom crash happened, and all the funding dried up. We basically went out of business. I mean, we did all the dotcom mistakes. We hired too many people. We rented an entire floor of an office building when we probably only needed like a room. We did all the classic dotcom mistakes. So yeah, that was my second business.

Keri: So, you know with every single thing we learn from it, right. You just said, okay, we learned, maybe we hired too many people, we have too much overhead, and that caused some of the issues. So now this is kind of like part two for you. At this point, are you like, I’m just going to go get a job, I’m done, this is too much? Maybe I did well the first one, maybe this isn’t right? Or was it, I have another idea, and I’m going to go and go after that?

Trevor: Uh no, absolutely, I decided to take a break. Actually the people I sold my company to where they’re like, we want to make it bigger, we want to take it to the next level, and you developed the first site, so we want you to develop the next one. So, they hired me back on as a contractor. So I was able to basically move from this failed company back to my old company. Then I just coasted for a while. That was the time when I moved to Asheville. I came up here. I went hiking in the mountains. I hung out with friends. I’d worked like 10, 15 hours a week. It was the nice cushy, relaxed life. So yeah, I definitely did not jump right back into it.

Keri: I think it’s important. I’ve had a few people on the show who have had multiple startups and multiple businesses like yourself. And they talk about that, there’s a difference, right? Like there are always successes, there are things that don’t work, sometimes you just need a break. How do you know the difference between I just need a mental break for right now versus this is not the space for me?

Trevor: I think it’s where your passion is. If you’re still thinking about it, even when you’re on the break, then maybe that still is your space, but if you take the break and you’re like, “Oh, I’m so happy to be away”, then maybe that isn’t the right space for you, right?

I think you kind of have to gauge it on, how much is it consuming you? That you have to do it versus this weight that’s lifted. If it’s a weight that’s lifted, then let it go. And then there’s also just the pure reality of recognizing–and this comes from our experience and talking to others who can help you analyze–is the market such, is the structure of your business such, that it will eventually, there’s a chance of it becoming successful, right? A lot of entrepreneurship is luck, but then there’s a lot of it is also skill and what you set yourself up for. So, the more that you can set up a business that is structurally set up for success structurally in the right market, the more that it’s better to stick with it. Even if you have passion, you should just give it up because it’s just, it’s never going to work out.

Keri: Well that brings me to the business you do now, which is Day Optimizer, and you know, I was reading a little bit online that you were talking about, you were doing all these things and you realized you had a process. You had something that worked for you. Can you talk about your transition into kind of doing something a little different than what you were doing before, but taking the skills and processes that you had to create something new?

Trevor: Yeah, I’ve always been about personal development and improvement, right? So, I’ve been writing goals and annual plans for years now. And actually, the genesis of Day Optimizer started in a business that I tried to launch–to go back to what we just talked about. When we talk about creating a business that you have passion for, but isn’t structurally sound.

The name of the company is called Strategic Life Tools, because my goal was to help people do better life planning and give them the tools to do so. So, I actually went and launched a whole business around this. I created a whole website with all these tools in a membership site to help people figure out: where do they want to be in five years? Where are they are now? How do they navigate that path? Right. Really trying to help give people the tools to do that.

But one of my constraints on myself, was that I really wanted to be doing a subscription business. My previous business was an enterprise software business, which means every month you start at $0 in sales, and then you gotta struggle to hit your target. And I sold that business to a company that was a SaaS business–a software and service business–where every month they started at the previous month’s revenue. Some people would cancel, but then they’d get new customers. So they could just like do this glide path up. And I said, that’s structurally how I want my next business to be. So I started this life planning business, Strategic Life Tools, and quickly found out that it’s very hard to get people to do planning on a monthly basis.

You know, I might like to do on a monthly basis, but I’m weird. Most people don’t. Most people do it, if anything, on an annual basis, right before the new year they’ll do their New Year’s resolutions. Or they do it at cusp events: they just graduated, they just retired, they just get divorced, they just got married. Something like that. Which is back to that one time sale sort of thing. So I quickly realized that was not the business I wanted to build, where it was going to be an uphill battle to build that business. And while I had passion for it, I couldn’t do it.

So during that I’d gotten a couple of initial customers and they were all struggling with time management. And, I realized that I’d been doing this technique that I’d invented like eight or ten years previous that helped me create a daily schedule, and it was a specific way of doing it. I actually created a tool in Strategic Life Tools to teach people how to do it. But then I said…that is something that I can make a business around. That is something that people are going to use every day that can really help change people’s lives, and I can build a business around that. So that’s what I’ve done.

Keri: And so what does that tool look like? What does it include? How do people use it?

Trevor: So first, any way that you can build a schedule, it’s gonna make you more productive. Because by building a schedule, what you’re doing is, you’re setting what psychology calls “implementation intentions”. And these are if/then statements. Like if I do this, then I will do that. And if you write those out in advance, you’re much more likely than to follow through. And a schedule is basically a set of time-based implementation intentions. So if it’s 10:00 AM, then I’m going to start doing deep work. If it’s 4:00 PM, then I’m going to start checking my email. Right?

So the start time actually helps reduce procrastination cause it creates this objective trigger, that makes it really hard to say like, oh no, I can delay working on this. You–at the beginning of the day or the night before–you committed to at 10:00 AM, you’re working on this. And it’s 10:00 AM. It’s hard to deny that without objective trigger. So it just nudges us to actually stop procrastinating doing it.

The end time gives us this moment of mindfulness. So one of the things people will often do is, they start doing internet research or any task and they get lost in it. And, they really should be stopping and saying: this isn’t the most important thing for me to be doing. Let me put this aside and work on the next thing. But if you set an end time, that’s this checkpoint. You can go, okay, is this the most important thing to do? If so, go, keep working on it. You should be working on that. But if not, that’s a signal for you to put that aside.

And then those two things combined, right? You create a start time and end time, or a start time and a duration, that gives you a time block. And that creates this scarcity mentality. And the way our brains are wired is when we have scarcity, we focus. That can be a bad thing because we often talk about the scarcity mentality with money, and that makes it harder for people to make longer term decisions around money. But when you’re actually trying to stay focused throughout your day, that can be a really useful thing.

So this idea of actually building out a schedule can help you reduce procrastination, increase your mindfulness and increase your focus. So that’s first about a schedule, and then I can explain the specific technique, but let me take a breather and let you ask any questions if you want.

Keri: I want to go back because one of the things that I have found from people I’ve talked to–whether it’s on this show or in other ways–is a lot of people have an issue with even figuring out what it is they want and how to prioritize it. So how do we kind of get those first two levels before we even get to kind of what feels like the third piece, which is what your product helps with?

Trevor: Okay. So I’m going to actually lead into then the three steps that we do because it will kind of answer some of those a little bit.

So my product is based around this process that I developed, which is this three step process for building a schedule. And the three steps are commit, allocate and schedule.

So commit is where you commit to what you’re going to do today, and the point of that is as a brainstorming step. So it’s like, what is everything I might want to do? When people are first starting out, I actually encourage them to be broader than they think. So you know, it’s like, okay, you have multiple competing things you might want to do, add them to your list, but things that you’re not going to do, just don’t. So just actually commit to doing several different things.

Okay, so now I’ve got my commitment list. Once this process is going, that acts as this way to focus. So if you have a normal task list and you look at it. It’s got like 30 things on it. That can be kind of overwhelming and it will distract you throughout the day. By actually committing and just pulling over what you’re planning to do, that will kind of narrow that focus. But if you’re going through this process and you don’t know what to do, then actually being broader kind of helps.

The next step is the allocate. One of the distinctions that Day Optimizer makes is the difference between time allocation and time estimation. A lot of times people worry about estimating the time for task and that’s figuring out how long the task is going to take. And for any sort of complex tasks that’s almost impossible, right? Something could take four hours or forty hours.

The thing that’s better is to allocate time. How much time am I going to spend on this today? So you can just say, I’m going to spend an hour on this and if I don’t get it done, great, I’ll work on it an hour tomorrow. That gives you a little bit more freedom to kind of just like block out and say, okay, let me adjust in the beginning, maybe just assign an hour to everything. If you don’t know what to work on, jump around and the passions will bubble up from there. But we’ll see in the next step, there’ll be a way to where you surface hidden desires through that.

So okay, I go through and I allocate all my times for everything. Now I go to the schedule step and I start building my schedule.

Well, we’re building our schedule visually, right? We’re actually kind of laying out and say, okay, this goes from 9 to 10, I’m doing this, from 10 to 11 through that. Now, if in the first step you actually threw everything on the schedule that you could possibly do, right? Like everything in the kitchen sink, you’re not going to be able to get everything on that schedule, right? It’s a fixed amount of time.

And so this is helpful for people who have problem prioritizing because one of the most useful prioritization techniques is something called paired comparison. It’s a bit of a complicated technique and hard to use, so people tend to not to use it. But the core concept of it is, it usually is much easier to look at two different things and say, am I going to do X or Y, then it is to prioritize a bunch of things and say, what is the top?

And so, if you fill out your schedule and then you look at the things that you haven’t scheduled and you go, I really want to do that. Then the question is, okay, what do you pull off the schedule? It’s a simple question. It’s just like, okay, what item am I willing to give up for that? Right? And that usually is a much easier question to answer than what are my priorities. It’s just simply, what am I going to commit to doing? What am I going to add to my schedule?

And then everything else–so in Day Optimizer if you were going through that process, there’s actually an uncommit button. Okay. I commit something in step one. Nevermind, I change my mind. I didn’t commit. So that basically is a useful way to do it. If you’re doing that on a paper planner, you can do that too. The idea there being that, like if you actually visually block out your time, you’ll be forced to make those trade-off decisions.

Keri: It makes sense. And I’m curious from a professional standpoint, so let’s say somebody is using this as a freelancer. One of the things that clients will ask for is, well how much time does this take, or they’re questioning the allocation of time. And you’re saying, well, don’t worry about the estimation of time, but kind of allocating a certain amount of time. But when you have a client that wants something done, how do you kind of use the system in that way?

Trevor: So this doesn’t replace normal project planning. If I know I’ve got a 40 hour project and I need to break that down into 10 steps and stuff like that, you’re still going to need to do your project planning to say, what are the different phases?

Day Optimizer works really well with other project management tools. This is more about helping you keep focused on a day to day basis. I think what a lot of people will do is they waste a lot of time during the day. They’ll stay unfocused, they’ll procrastinate, so that the project plan doesn’t actually get executed. But then the other thing that it does introduce is that it’s very hard for us to accurately estimate any complex thing.

Say that you are a freelance web designer and you’ve got a standard package where you say, okay, I’ll build you five webpages. And I’ve got that down to a science. Okay, you can estimate that fairly accurately. But say that you need to do a research report. There’s a lot of thinking you need to research and all that. Your variance could be up to 50%. You might think it’s going to take 20 hours, but it could take anywhere from 10 to 30 hours.

So the way to manage your time most effectively there is to make sure that you’re allocating time to keep moving that forward every day, and then still pay attention to your project plan. ‘Cause as it gets closer, you might need to drop other priorities. But this is more focused on managing your energy and time within the day, rather than on the larger scale.

Keri: Which is important, and I schedule pretty much everything. I love scheduling things, and I even schedule personal things as well because I’m sure as you know, sometimes if you don’t put it on your calendar, we don’t make it happen. A couple of the things that you do personally is you do swing dancing and you do barefoot running, which are two very different and interesting things. People who listen to this show know that I’m a dancer as well. I’ve done a variety. I’ve done a little bit of swing dancing. I enjoy it. What got you into doing swing dance and barefoot running and how do you make that a part of your schedule?

Trevor: Yeah, so swing dancing is interesting. So, my last partner and I decided to separate. But it was an amicable separation and we were looking for an activity that we could do together to stay connected. And so we saw a flyer for swing dancing and said, hey, let’s try that. We had tried salsa dancing a couple years before we didn’t make it work.

So we started swing dancing and after the first month, I think she quit and I just kept going. And now it’s nine years that I basically every week went, took a lesson and then danced afterwards and just kept learning. I started to going to the different dance camps and stuff like that. So yeah, and then the barefoot running is, interesting because it uses similar muscles to swing dancing.

With swing dancing, you’re kind of up on your toes. The posture that you use for swing dancing and barefoot running uses the same muscles. So I find running the conventional way, heel-to-toe, really difficult. It’s using different muscles for me. The barefoot running style where you’re, you’re kind of up on your toes while you’re running works really well. So yeah, that’s my different ways of getting cardio–to go out and run up the mountain, or to go out and do some swing dancing.

Keri: I love that. Of course I always enjoy anyone else that dances as well. So you add this to your schedule as well, right? You’ll put an allocation of time within what you’re talking about too?

Trevor: Yeah. So it depends. For swing dancing, what I’ll do is–because that happens at night–I’m just saying, okay, my schedule ends at 6, because the dance starts at 7 or something like that. So I just end the schedule.

But for running, my best time to run is like in the afternoon. I’m not a morning person. You’re not going to catch me running in the morning. My muscles are too tight. I like interweaving home life and work life. People talk about work, life balance, and there’s some people who like strict boundaries, there’s all work and then all play. I’m more of a weave-it-together. So I actually will schedule blocks in my day where from 2 to 3, I’m going out for a run. And then that helps make sure that I go out for a run because I committed to go for the run. So if I’m like, oh, I’m not quite feeling it. Nope. You put it on your schedule. You need to go do it. But yeah, I definitely schedule my runs.

Carrie: Do you have any advice for people listening? For those that really want to start a business, have an idea, but maybe are unsure or not sure of the next step they should take. What is your advice to them?

Trevor: One of the biggest things I think is talking to other people. I think a lot of times–and I was like this as well–early entrepreneurs, especially when they have an idea, they don’t want to share it with other people, they think like the idea is so special.

There’s this great formula, which is that success is idea times execution. And so even if you have a great idea, if you don’t actually do anything with it, it’s not worth anything. And the execution part is actually way more important than the idea. Every once in a long while you have this phenomenal idea that really someone else could take and transform the world. But more likely than not, it’s your execution that’s really gonna make the idea work.

And the way you get there is by sharing that idea with other people, getting the feedback and then iterating on it. And it’s the people who talk to other people and iterate on their ideas to refine them that actually are able to succeed. And then they also get the energy from other people to get motivated, to get started and things like that. So my piece of advice is always, is talk to other people and don’t be afraid of someone stealing your idea. Everyone has ideas, and people are all occupied about their own ideas and are very unlikely to steal your idea. Instead, go out there and figure out a way to make your idea work.

Keri: I agree, and I think a lot of times, I mean, there’s not really any new ideas per se. It’s kind of just how everybody puts it out. They do it in their own way. They do it in a different way, a unique way for their brand. So I like that. You’re bringing that to light as well. If people want to connect with you, they want to learn more, maybe they want to try out this product you’re talking about, where can they do that?

Trevor: They can try out Day Optimizer by going to DayOptimizer.com. They can also follow on Twitter @DayOptimizerApp, or on Facebook, just go to Day Optimizer. I’m on Twitter @FastFedora. Then if anyone wants to just contact me and email me a question about time management, entrepreneurship, whatever, they can email at trevor at day optimizer dotcom.

Keri: Perfect. And the last question I like to ask, all of my guests: what is one word or quote or mantra that you try to live by every single day?

Trevor: Make more mistakes.

Carrie: What does that mean to you?

Trevor: I think it means the way we learn, the way we grow, is by trying stuff and failing or making mistakes.

People have weird attachments to the word failure. But if you just say I made a mistake, you know, and then try it again and try it again, right? Making mistakes is the way forward. If you just jump into something, you’re going to make mistakes. You keep making mistakes, but then you improve. You fix those mistakes and then you make new mistakes. Then fix those mistakes. You need to make new mistakes. That’s the process of growth. That’s how we get better. And that’s how we develop expertise. That’s how we grow both in our business life and our personal life.

Keri: Well, this has been really informative and I congratulate you on another great startup that you’re doing and success you have. And I love that you dance as well. So nice meeting you, Trevor. Thank you for being here. And I look forward to hearing more of what you do in the future.

Trevor: Thank you so much. It was great to be here.

Keri: Thank you so much for listening to Ordinary People, Doing Extraordinary Things. If you’d like to be a part of my community, please join my email list to receive positivity in your inbox and updates on the podcast, as well as some other fun things by going to podcastcommunity.online. That’s podcastcommunity.online. And always remember that, yes, you matter. You are an extraordinary person, and that your life should be an extraordinary one, doing the things you love most and spending time with who you enjoy most.

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