What the Judges Say When a Poetry Company Applies to a Startup Accelerator

Rebecca Roach
Trubadour
Published in
6 min readJun 5, 2017
Hallway on the 35th floor of One Federal St., where the MassChallenge magic happened!

My work on Trubadour has recently hit an exciting high point: acceptance into MassChallenge Boston, a 4-month accelerator with some of the highest impact, early-stage startups in the world.

MassChallenge is, “the most startup-friendly accelerator on the planet.” I couldn’t be more excited and thankful for the opportunity. There’s a LOT to look forward to.

But, to be honest, I was shocked that they chose me, and Trubadour. I was surprised to be taken seriously, as a startup venture for poets and poetry readers.

Sometimes I feel like all I did was hold up “Poetry!” proudly on one hand and “Innovation!” on the other, and they said, “YEAH!” (This is oversimplifying of course, but essentially true.)

1500+ startups, spanning industries, applied this year — and only 128 got in. Was I selected because no other startup addressing poetry (I’m guessing) applied? Was I the “unicorn” that they wanted to take a chance on?

These questions have little relevance now, as bigger ones emerge. Like, for example, “how am I going to make this work?”

— I have no team. My excellent developer, Linus, is leaving for San Fran.

— I have no money. (At least not the amount necessary to accomplish what I need at this stage.)

— I have no design, tech/ programming, or sales/ marketing skills. (Trying, but fledgling.)

— I have no prior experience as an entrepreneur.

— And I’m currently living at home in the heart of the Midwest (Oklahoma), where it’s difficult to connect with the artists and business mentors I need to gain traction, build momentum, and get off the ground.

Hopefully the last concern will be mitigated as I move to Boston this month to participate in MassChallenge. But the other challenges are still very much looming. If I’m not able to satisfactorily meet these needs, and soon, the future of Trubadour might not bode well. I’m well aware of this, and I think that keeping in mind, “My company could fail before ever taking off,” is actually a healthy thing. (Bill Gates had a “nightmare memo” ready to send at all times to Microsoft’s inner circle should the worst happen. “Productive paranoia” at its finest!)

I think it’s important to be transparent, up-front, and genuine. Realistic, but also hopeful.

So, in the spirit of full disclosure, and for anyone interested in how a poetry startup (of all things!) is trying to grapple with the issues of “starting up,” I want to report the written feedback I received from the semi-finals round of judging for MassChallenge.

The 7 judges, with whom I interacted for 20 minutes on May 11, were angel or venture capital investors, cognitive psychologists, experts at large firms leading tech and innovation teams: an impressive array of industry professionals with doctorate degrees, accolades, decades of experience. (I know this because I read their bios before giving my pitch, to identify any potential conflicts of interest.) I was grateful for 140 of their collective minutes and for their thoughts and consideration in the deliberation stage.

Here are their anonymous comments (without the accompanying numerical scores for each section of the pitch):

You have incredible energy, passion, and smarts. You also have a major disadvantage — not being based in a thriving entrepreneurial hub (MC can help with that). It will be hard to build (much less scale) a business serving the needs of poets — the market size numbers you presented are very small. However, I do believe a) you are passionate about serving the community of poets / creators and will stick with it (i.e., revenue and successful exit is not your main motivation), and b) you will figure out, when the time is right, how to grow beyond the original “poetry” community. And even if you don’t, the impact to the poetry community will be sizable, and something that is aligned with MassChallenge’s mission. I’m giving you a high recommendation and hoping you are able to come to Boston, connect with the talent pool here, and adjust your plan and pivot as needed to serve the community, and (maybe even) create a successful business.

Excellent presentation. The financial model needs more work which would include data gathering on what people would be willing to pay. There could be a large play in using your platform for NLP [Natural Language Processing] and other applications. I agree to focus on poetry, but other applications need to be thought through along with other ways monetize the platform.

Love your passion and 100% believe you will create something amazing. I’d recommend trying to plug into more of the tech community, including connecting with folks who are already working in areas like natural language processing.

I love your passion for poetry. I think your goal of serving your fellow poets is noble. Your passion is infectious!

You definitely need your technical/business assembled. You will ultimately have to work with your team to better define how you are going to do this technically, and, of course, make it economically viable.
You may want to think about pulling in existing poetry content already available from Google etc.

You seem to be very enthusiastic about your opportunity. Your honesty about the unknown issues with your business model was refreshing. The opportunity with publishers is something it would be worthwhile pursuing as that represents a logical revenue source.

I deeply appreciate the energy for which Rebecca presented Trubadour. The market is unknown and the business is unconventional. The questions presented were challenging and the answers provided both authentic and honest. There are enough opportunities presented that have convinced me the effort is worth continuing.

Love the passion. As you build out your plans and vision, think about market size and how you can serve to the scale. There is potential to expand to other mediums that may make this more scalable. Take advantage of advisors and pick the right team. Good luck!

Yes, definitely some common themes: business model, market size, and scaling up by expanding into other forms of writing. The first one is the one I’m most concerned with. If we can prove that what we provide is valuable, I have confidence that the other things will sort themselves out.

And yes, passion. I’ve been living and breathing this vision since Jan 2016, and I guess I overlooked how deeply that has manifested in my life and thinking. When I talk about Trubadour, I just can’t help but convey how strongly I believe in this opportunity; it’s automatic. I underestimated the power of that.

So, if nothing else, passion is what I can provide this venture. Fierce, uncompromising belief in this vision and commitment to the task of helping poets and readers succeed.

I sincerely hope that’s enough to help me persevere and lead me to the right people for my team — and ultimately, to the right product.

Though I’m currently on my own with Trubadour, packing a couple suitcases and moving out to a big city in 2 weeks, I don’t feel without support. I’m optimistic that MassChallenge will lead to quantum leaps forward and upwards in our development. Thank YOU for supporting this effort, even by reading this post.

(And though I hate to mention it, on the off-chance that you’d be willing to consider another GoFundMe campaign, mine is here. A donation of ANY amount helps me a TON in actually being able to afford rent while I work on Trubadour full-time in Boston. Thank you for helping me follow — no, LEAD — my dream.)

Also, you can sign up for updates and new poems by emerging poets here. :)

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