Lessons From an Entrepreneur

After we graduated last May, Luke Berger and I began working for Cincinnati entrepreneur Alex Burkhart as we launched an Amazon Delivery Service Partner (DSP) Franchise. For context, in each major city in the US, DSPs operate Amazon Prime vans and rental vans that deliver packages to the local community. To meet Amazon’s targets, we had to grow our business to 30+ vehicles and 60+ drivers in the first 6 months of our operation. It was one of the toughest things I’ve ever done, but I learned so much and was exposed to the brain of an entrepreneur. I co-wrote most of this article with Luke. Here’s what we learned from Alex:

Get to the Deepest ‘Layer’ of Detail

Alex uses a system he calls the ‘Layers’ approach to evaluate the status of key priorities and projects to ensure that things are taken to the right level of detail. You can think of each layer as a step in the process of solving a problem.

Layer 1: The first draft. The MVP. You have something, but it’s in its earliest stages.

Layer 2: The first iteration. You’ve gone past layer 1, but still have a long way to go.

Layer 3: It works, but it’s average. It’s easy to stop here.

Layer 4: You’re convinced you have it, but then someone poses a problem you haven’t thought about yet and makes you realize you can still go a little further.

Layer 5: You have a great finished product, process, or idea that has considered every detail and stakeholder involved.

Going from nothing to something is an accomplishment. If you’ve started a business, written a blog post, or created a new process, it’s awesome to bring it into existence. But that’s only the beginning.

Alex challenged us to see our drivers as customers, and to consider them in every decision that we made. We were to put on a product manager hat and see the business as our product. Like a user experience designer tries to understand their consumer as deeply as possible, we were to view our drivers’ experience with the same level of detail.

If a driver was ever confused in their daily work, we hadn’t gone far enough. The same criteria was used to evaluate our new ideas and suggestions. If an idea we had could be dismantled by intelligent questioning, it hadn’t reached the 5th layer. Good managers have a knack for asking you the one question you hadn’t considered yet, forcing you to iterate again to get to that final layer of detail. Keep in mind that the law of diminishing returns applies to this system. Once you get to Layer 5, there usually isn’t as much value in spending many more hours to get to 6 and beyond.

Servant Leadership

Cynicism builds when a leader loses connection with those on the front lines. As 22 year olds managing drivers that were often many years our senior, we worked to make sure they felt that we were willing to work for them as much as they worked for us.

Alex came to our office to connect with employees and check on the status of our supplies on many Sundays. We hit the pavement and helped our drivers deliver packages in the summer heat. Having the mindset of a servant leader helped us build a connection with our people and kept us close to our ‘customer’ – our drivers. It’s not feasible for a CEO or manager to do every job in the company, but the willingness to jump into the field lets people know you care.

Find the Key People and Ask the Right Questions

I often wasted hours trying to figure out a problem by digging through piles of data or reading books about the subject. This desire to be self sufficient usually led to wasted time and the wrong answers.

Alex has a process of finding insiders within a business or industry, and developing a mutual relationship with them. It seems like he has a guy (or gal) for everything. I even witnessed him try to buy the domain igotaguy.com (to add to his list of other domain names…ask him about his dog business idea).

Luke and I learned that developing strong relationships with key players inside a business can help you navigate bureaucracy and get things done faster than trying to go it alone. You can do the same when trying to improve your business by reaching out to experts and gracefully asking for advice. Fostering these relationships and asking the right questions is more effective than keeping to yourself.

Become a Connector

Deals come from being social. Over and over, I witnessed Alex connect people who could benefit from knowing each other. This helps you to develop relationships with bright people and create new opportunities for yourself and those in your network.

I was fortunate enough to sit in on some of these connecting conversations, and learned about how to develop new relationships and build a solid social circle. I’ve started to work on doing this myself.

Be Willing to Operate In the “Grey”

In order to be effective, we had to live in an ambiguous environment. The right answers were never obvious. We found that obsessing over finding the crystal clear solutions in an evolving environment usually won’t lead to the right answers. 

At one point, I was obsessed with finding the black and white answer to two key problems in our business: creating the right attendance policy and hitting the delivery metrics we needed to reach our goals as a company. However, Luke and I were pushed to tolerate ambiguity and avoid building overly constraining policies for the sake of order. It led us to find success without needing to upend our initial processes.

“Don’t Assume”

This takeaway is a combination of asking the right questions and going to the extra ‘layer’ of detail. If we ever found ourselves assuming that we needed to go through the motions because ‘that’s just how it’s done,’ we were snapped out of it.

Luke and I found ourselves in new and unclear situations almost every day. It was easy to take things at face value for the sake of speed, but in many cases we needed to question our assumptions to get to the right answer. It’s easy to go with the flow without questioning the ‘why’ behind what you’re doing. Alex forced us to question our assumptions daily. It changed my mind about what’s possible in business.

“Money on the Wood Makes a Bet Good”

Luke and I were reminded that until the deal is complete and you have the money in your bank account, there are still places where things can break down. For example, it’s important to have a process in place to make sure that there were no mistakes made in your invoices or that you weren’t double billed on accident by a supplier.

When we were recruiting like crazy to hit Amazon’s ramp plan, candidates would sometimes ghost us at the end of the interview process or quit just before day one. We learned the hard way that until a driver was on the road delivering packages for our company, we couldn’t stop working to fill that spot.

A promise from a partner or new hire is one thing, but actually seeing that promise fulfilled is another. This doesn’t mean you shouldn’t trust people, but it’s dangerous to mentally mark something complete before the deal is officially done.

No Waste

Our culture was programmed to have a phobia of waste. Not because the $20 that was spent on buying the wrong phone case for one of our devices was going to make or break our business, but because the principle of frugality is important to remember.

At first, Alex’s waste paranoia drove me crazy. But I came to understand that if you misuse your resources in small amounts, a complacency sets in that causes more damage when there is more cash in the system.

Harness Your Impatience

Alex is not someone who likes to be confined to one task at a time. I can be equally impatient. He once shared a story about a mentor of his who suggested that he ‘harness his impatience.’ For those who struggle to focus on one thing, sometimes the best thing to do is find an outlet that enables you to use your restless energy in a productive way. 

For Alex, this means teaching an innovation class at the University of Cincinnati. For me, it means writing content like this, and for Luke it means hitting the golf course. To get where you want to go the fastest, it might be best to focus on just one thing. This was my mindset for a long time, but I’ve shifted my perspective. I don’t know if I could have my hands in as many buckets as Alex, but my experience in his world has made me open to doing multiple things at once.

Deliberate Work

Early on, it took Luke and I forever to complete tasks that eventually took minutes to complete. Instead of taking a step back and trying to work smarter, we spun our wheels. When you’re working long days, it’s painful to hear that it may be your fault for doing so, but Alex was willing to point out where we could improve. If you’re willing reflect on where you’re wasting time, it enables you to get more done with less.

It can be easier to put in 12 ineffective hours instead of 8 brutally efficient hours at work. I can’t say that it felt good to have Alex occasionally walk in and solve a problem in a few minutes that we worked on for a few hours, but it definitely changed our perspective about what’s possible. There’s a level of tenacity and focus that’s needed to get things done in less time. Luke and I got became much more effective over time when we pushed ourselves to get better at this.

Have a Bias For Action

Successful innovators seem to be willing to put something into the world before others would feel ready. They build the product or service as they go, using consumer feedback in the process. I learned that it’s more efficient to test a new idea before it’s perfect and then iterate as you go to get from zero to the “5th Layer” of detail.

I have a tendency to overthink the starting line because I want to avoid failure. I still have a long way to go, but being around someone who moves fast has given me the courage to do so myself, and I plan to take that into what I do next.

Have Fun

This is the lesson we didn’t take seriously enough. When you’re grinding, it’s easy to get stressed and cynical. If Luke and I have one regret from our experience over the last year, it’s that we didn’t have enough fun. Instead of enjoying the moment, we spent way too much time worrying about how things would work out. Even some of the longest, most difficult days could have been better if we had a different perspective in the moment. 

We went through some hilarious situations and threaded so many needles. We wish we would’ve documented the whole thing from day one. Nonetheless, we developed some strong bonds and got to know many of our drivers on a personal level. We proudly promoted two of our early drivers to become the lead operators of the company, and they’ve absolutely crushed it. We’ll have memories and lessons that we’ll never forget.

As someone with entrepreneurial aspirations, I plan to take these principles with me into the future. Not everyone wants to be an entrepreneur, but everyone can benefit from being able to think like one. I was fortunate to be put into a position where I could do so. Luke and I will always be grateful to Alex for this opportunity, and appreciate the growth we experienced in the process.

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