The Taming of the Tightwad

Dan Bender
Sep 4, 2018 · 5 min read

One of the hardest things I find about bootstrapping a company is deciding how to spend time and money. A handful of errors in how resources get allocated has the potential to set my partners and me down a path to the eventual demise of our livelihood. Being an accountant in a room full of free-wheeling creative types doesn’t help. Whereas I am hardwired to chase down every penny, my partners seem to have an undying belief that everything works itself out in the end.

When we started the company, I spent every spare minute dreaming about the moment free cash flow finally eclipsed our ability to pay ourselves something north of the poverty line. My partners, on the other hand, never questioned that our success was anything other than destiny and were happy to pour all available cash back into the business to keep it growing. I constantly worry about the downside risk while they seemingly shrug it off. It’s a major source of frustration for me, and the dichotomy fuels many heated exchanges inside the walls of Model B.

Whereas I am hardwired to chase down every penny, my partners seem to have an undying belief that everything works itself out in the end.

Thursday evenings are semi-sacred for us. That’s the time when the entire group comes together to discuss whatever is on our minds. Every teammate has a voice and the opportunity to be heard. Topics generally involve operational issues, aspirational goals, and tips on how to play nice together in confined spaces. It also serves as a helpful reminder that diversity in ideas and how you execute them is a very real thing. Given my reputation as a penny-pinching tightwad, when topics come up that revolve around spending money, it can sometimes lead to vigorous debate.

Not too long ago, someone on our team brought up the idea of doing some Pro Bono work for a handful of local charities. While I love the notion of helping those in need, I felt that we weren’t mature enough to take on that kind of commitment at the time. Why in the world would a young company that is bootstrapped and counting pennies choose to carry the weight of others? So, while I vocalized my opinion that we should shelve the idea until a more prosperous time, my partners enthusiastically embraced the idea and yet another deliberation ensued.

My consistent opposition to activities that cost us money has earned me a myriad of nicknames such as grumpy old man, little black raincloud, and Eeyore. In a way, I accept them as a badge of honor. I think my ever-watchful eye on the company’s finances is a healthy thing and so I’m happy to do it. However, I secretly wish I could be the cool parent and tell the kids yes, but my pesky conscience usually takes over, sucks away the fun, and mandates a hard no.

I secretly wish I could be the cool parent and tell the kids yes, but my pesky conscience usually takes over, sucks away the fun, and mandates a hard no.

I often feel like Katherina from Shakespeare’s classic play, The Taming of the Shrew. In it, Katherina is a miserable, obstinate woman. She argues constantly and, as a result, is viewed as undesirable by potential suitors. On the other hand, her younger sister Bianca is highly coveted. Katherina’s father insists that before Bianca may wed, Katherina must find a husband first. That sets off a wonderful series of twists and turns for which Shakespeare is so famous. Fortunately for me, my business partners and I got ‘married’ when we started the company and they didn’t have time to figure out that they should have been looking for a Bianca instead (suckers!). So there was only one thing they could do; attempt to tame the tightwad, like Petruchio did with Katherina.

For two years, my partners have been trying to reprogram me to be more like them. Sometimes it comes in the form of calm conversation, sometimes I get yelled at, and occasionally it’s innocuously suggested that I read a certain book in hopes that I absorb a fresh attitude (I’m on to you Abtin). Two years in and I’m as stubborn as I’ve always been, perhaps even more entrenched than I was before. To suggest that I have somehow changed and am no longer a tightwad would be a lie. But the thing that has changed is that I’ve learned to deeply trust and respect the people I work with every day. For me, that’s good enough to sometimes set aside my reservations and go along with them even though I really don’t want to. Hopefully the feeling is mutual, but if not, that’s ok too. We’re all well intentioned, we’re all in this together, and we all want to do things we’re proud to share with the world.

But the thing that has changed is that I’ve learned to deeply trust and respect the people I work with every day. For me, that’s good enough to sometimes set aside my reservations and go along with them even though I really don’t want to.

Speaking of things we’re proud to share with the world, we ultimately did choose to provide pro bono web development services to a number of amazing organizations including Main Street, Becky’s Fund and their Men of Code program, the DC Preservation League, and The Family of Austin Tice. Our very first employee, Ben Huizinga, was the one who pushed us to take on this kind of work and, in hindsight, we’re thankful he did.

I would encourage anyone reading this to take a moment and reflect on a couple of things. First, are there people in your life that you love and respect, but your disagreements get in the way of expressing that? If so, share this article with and let them know that having opposing viewpoints doesn’t mean you can’t have a healthy relationship and find common ground. Second, are there any charities or other causes out there that may be worthy of a little of your time and money? If you can’t think of any, I’d urge you to check out the four noted above as a good starting point. You never know where the road will take you.

Dan Bender

Written by

Co-Founder & Partner at @ModelBCo. Working with companies of all sizes & all stages on smart, sustainable financial management. DC to Greenwich to Aspen to DC.

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