Got It Wrong the First Time

I’m fortunate to belong to two super rad communities: the Subscription Box industry and the Midwest Startup community. One thing that I’ve learned from people far smarter and more successful than me is the importance of transparency and honesty in building a healthy, vibrant community. When you’re in the trenches of starting, supporting or working at a startup, hearing that your neighbor is having the same experiences can be validating. Sharing a load lessens the weight. When two people share the same problem and empathize, they can work together to solve it. Or maybe they just need to vent. That’s okay too! Sometimes a drink and a whine session with a pal are worth more than an Excel formula.

This is why I’ve never been too shy to share stories of failure, from how catering to our customers nearly killed our company to how we embrace failure in our company core values. For this post, I want to dive into three things I’ve faced as a Co-Founder at Bulu Box and where I got it wrong the first time.


Right person, wrong job


Sometimes, you meet a person who is so amazing that you just want them on your team. You want that person on your side so much that you hire them even if the timing isn’t right. The job doesn’t quite fit their skills, or you don’t define a role clearly for them. We’ve done this at Bulu Box. Inevitably, you have to let that person go, and it hurts. It hurts the person you hired, the team, sometimes the customers, and it’s hurt me.

I’ve learned to be brutally honest about jobs and expectations – so much so that it scares some people out of the hiring process. And I think that’s okay. It means that when you walk through the door of our office as an employee, you understand the framework of your position and you’re ready to kick ass.

At Bulu Box, we now use EOS Traction Tools (no, they don’t pay me to say this) to help us monitor if we have the right seats and the right people in those seats.


Not paying yourself enough

My wife Stephanie and I quit our jobs and poured our savings into starting Bulu Box. Yes, we did the whole “drain the 401K” thing, and yes, we knew that was dumb (we still have some left!). My fellow entrepreneurs will understand the feeling of “giving it all up” for the company, and that’s what we experienced at the beginning of Bulu Box. I’m grateful for the risk that we took; without going all in, I know that it would have been easy to walk away instead of being bold. Or perhaps it was by going all in that we had no choice, who knows.

But we didn’t understand that we needed to build our fair compensation into the growth plan of our company. The business model evolved, but we were still taking pay cuts to keep things going. I’m not saying that the Founders should be paid the most; however, there is a correlation between paying yourself fairly and understanding your value to the team. If the folks responsible for guiding and growing the vision of the company are too bogged down by the stress of non-work life, then it’s time to reevaluate because you need 100% of their brain power on the company.

My fellow Entrepreneurs, when you go all in, don’t forget to plan for yourself when you grow. Compensate yourself fairly for the risk (and debt) that you took on to launch your company and build your team. And if you see some success, don’t get greedy!


Lost in translation

Confession: I love goals. Fuck. I obsess about goals to a fault. My wife / Co-Founder and I are so into goals that we created a “Family Business Plan” from tools that we use for our company to build goals for ourselves. We have a family vision, mission, financial goals, etc. Crazy, eh? But goals are useless if there’s any ambiguity. Bulu Box is fortunate to have an Executive Board of genius business people (yes, that’s a shameless suck up), but even geniuses can have misunderstandings. Where I went wrong was not understanding that our core Bulu Box Leadership Team and our Executive Board didn’t always define success the same way. By Silicon Valley standards, customer growth at any cost is a success (see Blue Apron and Dollar Shave Club). By Midwest business standard, growth and users don’t matter if you’re not making a profit (usually). This misalignment created unnecessary tension and distracted from our shared vision.


“Sell more, faster” doesn’t work long-term to build a sustainable business. Make sure all parties are in alignment with what goals, success, and milestones mean for the company. Protip: create “S.M.A.R.T. goals” Specific (simple, sensible, significant). Measurable (meaningful, motivating). Achievable (agreed, attainable). Relevant (reasonable, realistic and resourced, results-based). Time-bound (time-based, time-limited, time/cost limited, timely, time-sensitive).

Do you dig this post? LMK what you love and hate via the comments below and I’ll stick with it!