Yup. I got into the digital agency business for dollars and sense. I had just left a startup where my full-time job was to care deeply: about the team, the product, the users. I needed a break from caring. I also needed to start affording real food again.

To that end, I started Topflight Apps LLC. I had a team of highly-skilled overseas developers and designers while building my own products. I knew I could manage projects and sell. Taking these disparate parts and forming a hired gun overnight, with certain margins no less, was a no-brainer of a play.

It was also a no-hearter.

At the same time, I lusted upon the $1 million ARR metric that all startups were taught to aim for. It’s a “focus on growth and condemn the bottom line” approach, taken to heart by Silicon Valley. When I started Topflight, I took refuge in this line of thinking that I should coldly calculate my way to victory this time by reinvesting in sales and marketing.

As I mentioned in my last post, I wasn’t completely wrong here. After being in business for 6 months, we’d exceeded our revenue goals and I had achieved a modicum of financial freedom where I can work where and when I want and still get myself an occasional hipster green juice. But along the way, I lost myself, and our company felt like an empty shell without a soul. We were taking on projects based entirely on hard numbers, rather than picking clients that we believed in and wanted to invest in. Tense discussions with my team revolved around the almighty dollar. As the saying goes, “Money is a great servant but a horrible master.”

When I got sick of this, I tried to fix the problem by changing myself. I tried to care more with client phone calls, advice, and going above and beyond the call of duty. But every single time, I felt guilty that these hours were taking away from things I should be doing to grow Topflight Apps. In retrospect, this was the right conclusion when I was handling stateside operations by myself. The problem was drawing the conclusion that “caring does not lead to growth”. Looking back, this was a scalability problem, not a caring problem.

Pretty soon, I was at a fork in the road: making Topflight Apps mean something, or making it a lifestyle business so I could split my time with something else that incited passion again. I gave a serious look at a building a healthcare SaaS product and also a project management gig for my dream healthcare company, both of which would also put me right back in the “gotta care” slot again.

I’m not gonna lie and say that what happened next happened at all according to plan. What it did do was reinforce my belief in karma and save the company’s soul.

Hiring For Who Was My Luckiest Move Ever

In November, I started recruiting a stateside team for completely pragmatic reasons. I knew that having stateside project leads would build credibility, communication, and trust with stateside clients. Because this job requirement had more to do with these intangibles than skills, I based these early hires 50% on Who and 50% on What. I hired 2 full-stack developers, Jacob and Nezare, and a designer, Jack, that were all elite at their craft, but they also happened to be people that I would co-found a startup with and stop everything to help if something happened to them.

The business move made sense. With this team, we were able to convey “we got this” to get a second look from clients that gave us cold shoulders when it was just “Joe and overseas devs”. But little did I know, I had also introduced a Trojan Horse that would break down all the hardened walls around my wee heart.

They Introduced Caring Like A Trojan Horse

Enter Jack, Nezare, and Jacob. Even though they all work in different capacities and technologies, their job can be described simply as….to care. Jack delivers UX and UI prototypes that allow clients to demo to investors after spending a couple k on us, and he wants every design he touches to win awards. Jacob takes ultimate pride in validating what we build and QA-ing everything himself so clients with production needs can rest easy. For Nezare, he turned down a 6-figure job to work with us because he gets to take on more challenging projects, which has led to Topflight  offering the most bang-for-buck for machine learning that I’ve frankly ever heard of.

For every action there is a reaction. It may not happen right away, but truthfully it happened fast. Within 3 months of hiring them, clients responded in the following ways:

1) Clients peeled back the skin to reveal larger budgets over time.

2) Clients started ASKING to be billed for communications. (Seriously.)

3) Clients started referring us, and the network effect is the gift that keeps on giving.

In every way, making our team’s job to care about our clients has been a positive return. We haven’t spent a single dollar on sales in 2017. All of our current clients have been going strong with us since last year, and we’ve hit our revenue goals each month. Everyone is getting a raise. Most importantly, we love what we do. The trojan horse effectively turned what started as a dollar and sense into a company that gives us the purpose we crave. What’s better than changing the world one project at a time? Changing the world many projects at a time, and still being able to pay my team’s bills.

How My Team Changed How I Lead

As a CEO, at the end of the day, the tension between caring, and making sure the company is stable enough to dole out stable paychecks, will always exist. So I had to figure out how to contribute to and even strengthen a business where what we’re selling is “we want to go all in with you!” I believe the answer is in how I treat my team. How can I create an environment where my team wants to experiment knowing they may fail, learn new skills to help a client, and take total ownership of whether a client’s project fails or succeeds?

Some of the things I’ve tried (and credit for many of these ideas go to the team):

* asking them to bill me for everything minute they spend, including communications and learning;
* buying them books (especially on product design, lean analytics, and validation) that would allow them to offer advisory value on top of technical insight;
* taking time every week to give and receive constructive feedback (must be 2-way street);
* sharing honestly in a team journal jam packed with personal frustrations and group resolutions (think group therapy where titles don’t exist);
* pushing them to try new roles within the company (because they’re rewarded not penalized for learning curves, they take on new roles with glee);
* checking into their personal lives and genuinely caring about them;
* …. and saving the cheesiest for last, trying to focus on the positive especially when I’m tense about financials.

In summary, I’ve tried my darndest to, when faced with a decision to focus more on growth in numbers or growth in my team, always pick the team. This is the rising tide that appears to be lifting all boats.

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