Published Together: Failing in public hurts. Moms can heal.

A little over two years ago, I wrote about a moonshot mission to civilize how people think of and discuss current events. Not just any old current events; we thrived where division flourished, covering topics like gun control, immigration, COVID-19, and more. Our product was geared toward middle and high school social studies teachers. The idea was simple: get people talking and engaged before they become lost in the echo chambers that rule our news and information streams.

It was satisfying work. Not only that, but it was a fundamentally good idea. The problem is that good ideas don’t automatically mean good money, and startups can only run on sheer willpower for so long. The mission was there, but the execution and product implementation weren’t.

After two wonderful, agonizing years, we made the decision to shut Civil down in November 2022.

Mistaken assumptions

With hindsight as my unerring guide, it’s clear to me now that my team and I should’ve focused more on validating the foundational assumptions that would dictate the success or failure of our venture.

First, we assumed that teachers wanted to dive into current events but were unable to do so due to a lack of materials, training, or other resources. Second, we felt that if we got teachers on board, they could (and would) go to their administrators and lobby for purchasing funds and schoolwide implementation. As you can probably guess, neither was as true as we thought. 

Did teachers want students to leave their classrooms as informed, critical-thinking civilians? Absolutely.

Did they want to brave the topic of gun control or immigration with a room of 16-year-olds? Some, but not nearly enough.  

To be clear, I don’t blame them for that. Teaching is hard enough as it is. We heard one thing and refashioned it to fit our narrative. It took us a couple of years to fully realize our blunder.

We also assumed that teachers could rally administrators behind our product, which turned out to be a fool's hope. We tried as well, of course, to no avail. Legions of investors and advisors told us selling education technology was a challenge. Unsurprisingly, like many headstrong 20-somethings, we were convinced that a team and mission as inspired ours would break through.

Not only did we fail to reach the mountaintop, but this company that had become an integral part of our identity died. That’s the part of the startup journey that doesn’t go viral on LinkedIn.

Facing up to failure

For a while, you can feel ashamed of your failure and embarrassed that you took so many people along for the ride. Time helps you see that everyone knew the risks involved, but it took me a while to get over that. 

The lethargy and apathy that followed the end of that chapter were acute. I was depressed and spent many days rotting in front of my TV. Yes, I got through five seasons of “Suits” in two weeks, but at what cost?

Two years out of college, I was fortunate to be still living with my parents at the time. The free rent and groceries gave me the latitude to grieve. That process was shepherded by my then-coach and now friend, Jason Pliml. He encouraged me to simply be sad, fully experiencing my emotions instead of burying them in work, substances, or other vices. Without him, I might’ve jumped into the next venture without truly processing the passing of my proverbial child.

While all that was going on, I’d also been following Twitter entrepreneurs running “sweaty start-ups”; mom-and-pop small businesses that eked out a competitive advantage with an infusion of basic operational and marketing tech.

I watched as self-storage, pool cleaning, and house cleaning companies grew and seemingly overtook less efficient incumbents who still relied on Rolodexes, in-person quoting, and derelict websites.

Trying a new idea

In August 2022, with Civil’s financial runway deteriorating, I started thinking about giving one of these sweaty startups a shot. I had already gotten over the scariest stage of entrepreneurship – just starting the damn thing – out of the way with Civil. Plus, I couldn’t get much more broke.

I approached my mom (and then housemate), Jenn, who was leaving a nonprofit leadership role after her relationship with the president soured. It wasn’t her startup per se, but she’d devoted years of her life developing a team at an organization she planned on retiring at. 

Knowing how hard she and I were taking the sunsetting of our previous professional aspirations, I asked her if she might want to start a residential cleaning company. I thought it’d be a fun side project to work on together. For me, I was seeking a bridge between Civil and whatever came next.

After some initial ideation sessions, we started our venture. Still, I was still very much grieving the end of Civil. At first, I drifted along in Jenn’s wake as she provided most of the horsepower that launched our joint venture: Keep. A Cleaning Company. 
Honestly, I don’t know if I’d still be a part of the company if I were working with anyone else.

She had every right to build the company up while I wallowed, then look back on the inequitable amount she’d contributed compared to me and try to box me out. But she didn’t. Jenn knew I was in a rough place and (correctly) calculated that, given enough time, I’d come out of it with fresh motivation to grow our cleaning business. She applied her professional skills and tended to my needs because of her compassion for me as my mom. 

That’s the sign of a great teammate, right? Picking up the slack when your partner doesn’t have the willpower to do it themselves while acknowledging the different skills each brings to the table.

Building a firmer foundation

Our relationship and shared experience supercharged that dynamic when our fledgling startup needed it most. That’s one of the reasons working with family can be so powerful, especially when borne out of an intergenerational relationship like ours.
While it is true that Jenn did most of the heavy lifting for the first few months, I don't want folks to think I was completely useless. I was determined to avoid the same mistake we made with Civil and ensure, to the best of my ability, that we weren’t building on a shaky foundation.

Step one: investigate our potential competition. We called at least 15 cleaning companies in Grand Rapids, and only three actually picked up the phone. Then, we tried to book cleanings online and noted that just one company had let us book online. From the standpoints of  customer experience and ease of booking, our competitors were vulnerable.

Step two: validate the demand for house cleaning services. There’s a catch though; the only way to do that was by putting ourselves out there and seeing what happened.

Here’s where many aspiring entrepreneurs I’ve spoken to get tripped up. Analysis paralysis is a real thing, and it’s so easy to put off taking the leap by doing market research, creating business plans, and doing other positive things that don’t take the place of actually putting something out there. 

So, we created the first version of our website, and we were off. By January 2023, we surpassed $10,000 a month; today, we’ve grown to over $70,000 a month.

Taking the leap

If you feel like you’ll never recover from whatever just happened, are scared to take the entrepreneurial leap, or are worried about what people will think of you, I understand your pain, anxiety, or embarrassment. 

On business No. 2, I still struggle with imposter syndrome. “I failed once; what’s stopping me from failing again and showing everyone who I really am?” The reality is that imposter syndrome is indicative that you’re in the right room, not the wrong one. That feeling of discomfort is a blessing in disguise. It’s a sign that you’re pushing yourself out of your comfort zone and growing.

The reality is that people care way less than you’d think, and you’re capable of more than you know.

Take time to feel your emotions, but don’t let them cripple you permanently. 
The only way you truly fail is if you don’t learn and grow from your experiences, failures, successes, or otherwise.

Thanks, Mom

This Mother’s Day, I’m here to say first a thank you to Jenn for being my business partner and mom. It’s a privilege to have her as a part of this journey.

Working with one's mom is certainly not for everyone, but, based on my experience, I challenge you to thoughtfully explore and not fear a potential venture with a family member. 

Returning home gave me a renewed relationship with my mom and helped create a profitable, sustainable business that will support both our families for years to come.

"Published Together" is Rapid Growth's version of the Op-ed and is ushered forward via community conversations held first with our Publisher Tommy Allen.

Max Tendero graduated from the University of Michigan in 2020 with a degree in political science. After Civil, he founded Keep. A Cleaning Company with his mom, Jenn Tendero. Keep serves West Michigan from Grand Rapids to Muskegon to Kalamazoo.
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