Trevor Lohrbeer is a serial entrepreneur working on his fourth startup, Day Optimizer. Day Optimizer is a desktop & mobile web app that helps you mindfully plan your day by walking you through a 3-step process to convert your daily to-do list into a daily schedule, so you can accomplish more.
Prior to Day Optimizer, he co-founded Lab Escape, an enterprise data visualization software company that he sold in 2015. Lab Escape’s customers included Walmart, Dell, Schlumberger and the U.S. Army.
Before Lab Escape, he co-founded True Peers, a social network for professionals that folded after they failed to raise additional financing after the dotcom bust and Slambook.com, a home page add-on service he sold in 1999.
Trevor’s side projects include:
– Lean Decisions
A blog aimed at helping people use the minimum amount of information and process needed to make successful decisions.
– Strategic Life Tools
A free membership site providing life planning tools to help people live a more deliberate life.
– Fast Fedora
A personal blog covering Trevor’s interests in analytics, decision-making, professional networking, business and technology.
Trevor can be found on Twitter at @FastFedora or @DayOptimizerApp, or on Instagram at DayOptimizer,
Trevor splits his time between Asheville, North Carolina and Berlin, Germany.
Where did the idea for Day Optimizer come from?
After I sold my last company, I started working for the acquirer. While thinking about what I wanted to do next, I wrote the following short tool:
> In my __(work/personal/volunteer)__ life, I help __(who do you help?)__ to __(what do you help them do?)__.
While my new job was interesting and I was working with great people, how I filled out the tool wasn’t inspiring:
> In my work life, I help online retailers sell more stuff.
That clarified for me that I wanted more meaning in my work. I wrote what I wanted the sentence to say as:
> In my work life, I help people to live more fulfilling lives.
From this spawned the idea of Strategic Life Tools, a web site that helps people make life plans. I built an initial set of 8 planning tools and launched the business before realizing that I wanted to build something that people used daily.
So I made Strategic Life Tools free and took a technique I had been doing on paper to help me plan my day and built the Day Optimizer app around it.
What does your typical day look like and how do you make it productive?
While the typical advice for success is to wake up early and have a strict morning routine, I have never been able to make that work for myself. I am naturally a night owl and don’t do well with fixed routines.
Over the years, though, I’ve learned the psychological tricks that do work for me: scheduling my tasks at specific times, limiting my work using time blocks and creating streaks that I don’t like to break (Jerry Seinfeld’s Don’t Break the Chain technique).
Nowadays, I wake up around 8am and use Day Optimizer to build out my schedule for the day. I work in time blocks of no more than 90 minutes and intermix my work with activities like meditation and exercise. I use the mini-deadlines created throughout the day by my schedule to drive my focus—when I know I only have an hour for a task, I get started on it faster and get distracted less.
The net result is that I’m far more productive on the days when I create a daily schedule than on the days when I just work from a task list or wing it.
How do you bring ideas to life?
I start with trying to fully map out the problem. That involves a lot of brainstorming of the potential ways people approach the problem and how they might solve it.
Next I develop a conceptual framework that I feel accurately captures the problem and potential solutions. Usually I’ll refine this framework by talking to others, looking for the gaps and where the map doesn’t match the territory.
During this process, I will often sketch potential solutions out on paper, drawing what the user interface could look like and thinking through the flow.
Once I have a decent understanding of the problem and ideas on how to solve it, I will build out prototypes within a branch of the software itself. Much of what I focus on is getting the details right, and it’s only in the implementation that those details come to light.
Often, after going through this process, I discover that I got something wrong and have to throw away all my work and start from scratch. For me, this is a cost of the work I do. While I often release incomplete implementations that will take more work to complete, I shy away from releasing work based on an incomplete or wrong conceptual framework, as that often leads to tech debt that is hard to recover from.
What’s one trend that excites you?
I’ve been following the development of AI for years now, and the pace of change has been incredible. I both excited and fearful for how AI technology will impact our world, technologically, culturally and societally.
For those who want a quick overview, Two Minute Papers is a YouTube channel that posts regular 2 minute overviews of AI research and news. The videos can sometimes be technical, but the videos do a good job of giving you the breadth of the impact of this technology.
What is one habit of yours that makes you more productive as an entrepreneur?
Creating a daily schedule that includes all of my tasks, appointments and activities for the day.
I know that can sound a bit promotional, since that’s what my app Day Optimizer does, but I truly believe in the technique. I’ve been scheduling my days on and off for years, well before I started building the app, and there’s a huge difference in productivity between the days I do it and the days I don’t.
And, since I’ve started working on the app, I learned that scheduling your tasks into your day is a type of “implementation intention”, which research shows increases the chance of goal attainment.
If anyone wants to try the technique, I created a tutorial on how to do it on paper or in Excel here. Day Optimizer adds a few things to make it easier, but the technique can be applied in many forms.
What advice would you give your younger self?
When building your network, focus on those people you enjoy spending time with and aim for quality over quantity. One person who you have a deep bond with, who understands your needs and desires and who truly wants to see you succeed is worth ten people who are only casual acquaintances who don’t have any emotional investment in helping you.
Also, ask for mentorship early. Get into positions where you can learn and connect with smart, motivated people. Don’t just hope you’ll learn from being in the same office as them—find a way to work with them on a regular basis.
Tell us something that’s true that almost nobody agrees with you on.
There is no utopia to reach, no steady state for society. The world is a series of trade-offs that we make as a society, and as society evolves, the choice of which trade-offs we need to make does too.
As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?
Never stop learning and improving. Never think you’ve mastered it all. There is always more to learn, more depth to gain in subjects. Everyone has something to teach you if you look hard enough. So look hard, be interested in everyone and everything, and keep making yourself better.
What is one strategy that has helped you grow your business?
Create a hypothesis of some aspect of your business: your marketing message, the next feature your customers want or the best place to find job candidates. Then construct an experiment to test that hypothesis.
I’ve most recently run experiments using Google Ads to determine the current iteration of my marketing messaging, using a technique where I test 3 messages, each with 3 copy variants (for a total of 9 headline variants), then look at the click-through rate for my target keywords to see which messages resonate the most.
My favorite talk on this subject is “The Scientific Method: How to Design & Track Viral Growth Experiments” by Brian Balfour of HubSpot. He explains how to think to develop a process for growth.
What is one failure you had as an entrepreneur, and how did you overcome it?
In 1999, I co-founded a dotcom with 5 other co-founders. We raised $500,000 in an angel round on the idea of a job auction, then pivoted to a social network for professionals (similar to LinkedIn, but we failed before they started).
The failure was getting caught up in the dotcom madness. At our peak, we had 13 employees, an entire floor of an office building and no revenue. After the crash of March 2000, we were never able to raise our next round of funding, and though we ran on fumes for another 9 months, we eventually folded.
What I learned is that failure is rarely devastating. Even in this case, where we had to shut down the entire business, I learned a lot, and I found a job to support me until I was able to start my next business.
A frequent question people ask is “What will you do if this fails?”. I like the response I learned from someone a long time ago: “If this fails, I’ll just do something else.”
What is one business idea that you’re willing to give away to our readers?
A Software-as-a-Service review system that provides personalized ratings and scenario-based reviews for any online product or service.
The personalized ratings are simply ratings calculated for each customer, based on how they have purchased or rated other products in the past. So instead of a product being 3 stars, it might be 5 stars for you, but 2 stars for someone else.
Think Amazon’s or Netflix’s recommendation engines, but provided as a service for any SaaS company. This can be achieved using a simple market basket analysis and would make existing review sites for travel, restaurants and other products much more useful.
Scenario-based reviews don’t aim to answer how good or bad a product is in general, but rather under what conditions a product is good or bad. What is perfect for one person may be horrible for another. By focusing on “fit”, reviews can be provided for specific scenarios.
What is the best $100 you recently spent? What and why?
The Logi ERGO K860 split ergonomic keyboard.
People don’t spend enough time or money on getting a proper ergonomic setup for their computer, but I believe it’s critical to aging well in the digital age. Sitting slouched at a laptop staring with your head tilted down typing on a cramped keyboard will catch up to you as you age.
I’ve had an ergonomic setup for years, but recently bought a new laptop and was having to plug and unplug my corded keyboard whenever I switched machines—a huge hassle.
The Logi K860 supports up to 3 computers via Bluetooth. Using the Logi Flow software with the Logi MX Master mouse I already have, I can now simply move my mouse between computers and the keyboard automatically switches, instantly improving my productivity.
What is one piece of software or a web service that helps you be productive?
Not to be too repetitive, but my own software Day Optimizer provides the biggest productivity boost for me. Using it to schedule my days is now one of my foundational practices that enables me to prioritize what is important and stay focused on that throughout my day.
After that, the other app that I use daily is [everyday.app](https://everyday.app/) to keep track of my daily habits like meditation, exercise and learning German.
What is the one book that you recommend our community should read and why?
“Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses” by Eric Ries
Lean Startup teaches entrepreneurs techniques and concepts to create a rapid feedback cycle for iterating a new product and finding the right market for it. Many of the techniques were in use before, but Lean Startup crystalized them, making them accessible to a much greater audience.
While many of the terms, like Product-Market Fit and Minimum Viable Product have become part of the general business lexicon, they are often used incorrectly. Reading Lean Startup will give any entrepreneur clarity and deeper insight into the meaning behind those terms and how to use the techniques taught by the book.
What is your favorite quote?
“Life shrinks or expands in proportion to one’s courage.” – Anaïs Nin
- Schedule your tasks at specific times to reduce procrastination & timebox your activities to increase your focus.
- Build your network with people you enjoy spending time with.
- Spend extra time to understand a problem upfront before you attempt to solve it.
- Run experiments to figure out what works and never stop learning and improving.
- Don’t be afraid to fail; failure is just an opportunity to do something different.