What do you do when you’re struggling with a company you love? Two co-founders are at a turning point with their careers, their dream & their lives. As an experiment, they’ve decided to be totally honest with themselves, their users & the world for 30 days.

Jess and Erin birthed their baby launched Dabble in May 2011 in Chicago. Like most entrepreneurs, they’ve found the ride to be exhilarating since then. Ups and downs. Sometimes lefts and rights. Tears and celebrations.

As founders, Jess and Erin now find themselves at a critical point at deciding the fate of their dear Dabble.

The good news? Dabble has helped thousands of people shake up their routine and try something new. We’ve raised two angel rounds of funding and grew to a great, quirky culture with a team of seven people.

The bad news? The business is not yet profitable, and we’ve reached the end of our runway. We’re now two co-founders (unpaid) and one amazing team member (paid), trying to figure out what will happen next.

So as an experiment, for the next 30 days, we’ll be trying to figure out how to keep Dabble alive and document our entire journey. Not only for ourselves – but for the sake of our students, teachers & investors.

What we’re facing is not unusual in the life of a start-up.

What’s unusual is the decision to share this predicament with our community. We’ve commiserated with many others in our shoes. We’re doing this project to lay bare what we think isn’t done enough: brutal honesty when it comes to building a company and pursuing your passion. We don’t think we’re alone in this struggle.

You can find out ways you can help or ask a question.

Why this Format? Why 30 Days?

Have you guys come across the site Forty Days of Dating? It pretty much grips you at your core. You feel what they feel. It’s done beautifully. We felt a similar format would help us accomplish our goal of honesty. We’ll likely be switching up the format as we see where the project takes us, but for now it’s a way to start. Why 30 days? Well, it’s arbitrary.  In start-up life, though, 30 days equals A LONG TIME. A lot can happen in a period of 30 days.

Who We Are

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About Erin
Erin is a Dabble co-founder based in San Francisco. A former marketing strategist, Erin left the comfort of a corporate job three years ago to try her hand at entrepreneurship. She is the realist of the two, having more grounded expectations about where Dabble can do without a miracle.
LinkedIn | Instagram | Twitter

Questions for Erin

Why are you participating in this experiment?

I’ve thought a lot lately about the notion of honesty. I’ve struggled with the idea that we must “fake it ‘til we make it,” and putting on different faces for different interests. The times I’m feeling best about what I’m doing is when I speak from the heart, “hey, you know, turns out things AREN’T going so great.” This vulnerability tends to prompt a real conversation that becomes more meaningful to both people.

Do you like running a business?

Yes and no. (Is that cheating?) I like the freedoms it has afforded me in my schedule, and the fact that no day is dull. (I can’t remember the last time I looked at the clock and thought, “man, I can’t wait for 5 pm.” Usually it’s the opposite, and I want time to stand still so I can get more done.) But I don’t like that I’m in my head more than ever, I’m constantly feeling like I’m not doing enough, and I question every decision.

What’s the best thing about working on Dabble?

The fact that we’ve created this thing that has tickled and delighted people. On days that may not be going so well, it helps to turn to the class reviews, or the every-so-often “love letters” from Dabble fans that turn up in our inboxes. We set out to create a solution to a challenge we both faced, and it’s awesome that so many others have enjoyed our solution, too.

Why isn’t Dabble working?

We don’t have enough awareness. Since we’re taking 25% of every ticket, and the average class costs $30, our business model is only profitable at scale. And the reality is, we’ve grown eight-fold in Chicago, but it’s not nearly where we need to be to reach profitability.

What’s difficult about your current situation?

I believe wholeheartedly in what we’re doing. I think its potential is massive. The most difficult thing to swallow is thinking that a few wrong decisions or a stroke of bad luck may crumble it. The “what ifs” that keep me up at night. At this very moment, it’s also difficult that we’ve taken a step back from where we were six months ago; having to cut the team in half because of lack of capital has not only changed the dynamic of our awesome culture, but also changed what we have to focus on on a day-to-day basis, just as we were becoming a more well-oiled machine.

How has it been working with your cofounder?

Jess and I have been working together now for three years. And on Dabble for two and a half. I AM SO GLAD I HAVE A PARTNER IN CRIME. Seriously. My first reaction to solo founders: “wow, I really admire you.” Though as cofounders, you certainly sign up for some conflict as you definitely won’t agree on everything, in my opinion, the advantages outweigh the negatives. In recent months, Jess and I have realized some differences in vision for the company. At the same time, we’ve been under more stress what with approaching the end of our funding runway. This equation has certainly caused a few disagreements in recent months, but at the end of the day, I couldn’t ask for a better cofounder to be traversing this messy adventure with.

What do you hope Dabble accomplishes in the world?

I hope one day “let’s Dabble” becomes part of the lexicon. People are dabbling a few times a month or more. Dabble becomes the default for an unscheduled week night – or lunch hour. Dabble is responsible for inspiring career changes, unlikely friendships, and even a few marriages.

What do you hope Dabble allows you to accomplish?

I hope Dabble expands my horizons both personally and professionally. I can already say that it has. But ultimately, no matter what happens with Dabble, I know I’m a much stronger person for having done it. I hope it opens up doors for me in the future.

What’s the worst thing that could happen?

The absolute worst thing that could happen is that we have to shut Dabble’s doors. And potentially piss people off? To the point that our reputations are at stake? (Did my mind wander too much there?)

Are you nervous about this experiment?

Yes! I’m relatively open with friends and those close to me, but I’ve always struggled with completely putting myself out there… on the internet. (Just typing that made my heart beat a little faster.) Not all will like what we say, and the people pleaser in me finds that a little stressful.

About Jess
Jess is a Dabble co-founder based in Denver. A former urban planner turned entrepreneur, Jess loves building things and advocates for great design and user experience. She is an eternal optimist and believes Dabble can survive against most odds.
Linkedin | Instagram | Twitter

Questions for Jess

Why are you participating in this experiment?

I think I’m excited about putting everything out there. The good, the bad, the ugly. I believe Dabble needs to exist in the world – but we definitely have some big issues that need to be sorted out. It will feel great to let our community of students, investors, teachers & hosts know what’s happening in an open, transparent way. I hope we can rally support and feel great about the next chapter of Dabble.

Do you like running a business?

I do. I’ve been in the entrepreneurial world for 5 years. There’s things I miss about the corporate world (namely predictable paychecks) but I wouldn’t give up working on something I love for that. I get to decide where, what & how I spend my time each day. I get to build something that matters to people. One complaint – it’s sometimes difficult to separate Dabble from my personal life. I’m still working on that.

What’s the best thing about working on Dabble?

I am not a typically emotional person, but I get teary-eyed when I hear stories from teachers & students about the impact that Dabble is having on their life. It’s awesome. Also the freedom to have Dabble as a creative outlet. Coming up with new ideas. Building them. Collaborating and working with awesome people. Freedom to set my schedule and put family & life first. That’s what matters most.

Why isn’t Dabble working?

It’s really hard to answer this question – because it’s working on so many levels. But honestly, it’s not working because we’re not making enough money to support the business sustainably. We’ve supported ourselves with outside funding until now, but we’ve reached the end of our runway with no funding prospects – so here we are.

What’s difficult about your current situation?

Erin & I have poured a ton of ourselves into Dabble. We love it. We believe in it. It’s hard to admit that something isn’t working as well as we had hoped. We’ve tried a lot of different things to grow Dabble. Did we failed at some point? Did we miss something? Could we have done better? What could we do differently now? These are the tough questions (with no answer) that I ask myself daily.

How has it been working with your cofounder?

I’m so glad Erin & I are in this together. We’ve been through so much and still get along well – which is ridiculous. Plus, the stress would have killed me if I was doing this by myself. We’ve been through hiring, firing, fundraising, ups & downs. Erin keeps my head on straight. I’m naturally impulsive and she reels me back to think about an initiative from all angles. While we have differing opinions on some things, we definitely make good business partners.

What do you hope Dabble accomplishes in the world?

Oh, so much. I hope Dabble is the spark that helps people stop talking and actually DO the things they are passionate about. I hope it inspires people to create, laugh & meet their neighbors. To find balance. To try something new. I feel like for the first time in my life I’m working on something that is so GOOD. It helps people. My ultimate goal would be to see it continue to grow and help people around the world.

What do you hope Dabble allows you to accomplish?

For me, it’s all about passion, challenge & flexibility. Passion for the work I’m doing. Feeling challenged and invigorated by the road ahead. The flexibility to actually have a life outside work and ability to put my family first.

What’s the worst thing that could happen?

The worst thing that could happen is that Dabble goes away. We fade off into the sunset. That would be the worst thing. Erin & I will do everything in our power to ensure that doesn’t happen. We’re here because we’re trying to find a better way. I believe we can find a better way.

Are you nervous about this experiment?

Yes. I’m getting married in a month. We have no idea where this experiment will take us (which is exciting) but it’ll definitely throw some curveballs in an already stressful time.Also, I don’t particularly like being vulnerable. It’s really nerve-wracking to be putting our dirty laundry out for the world to see. But if we’re able to rally support or at least give Dabble a better chance at survival, it’s all worth it.