The Compare Game For Startup Community Leaders

by Chris Heivly, Entrepreneur in Residence at Techstars

My children are all adults now (that does not mean I am done being a parent) and I am reminded of one of my pet peeves that siblings seem to do all the time. That pet peeve is complaining about what they did not get as compared to what their sibling received. I used to call it the compare game and my kids all knew that was a hot button for me and thus to not use that in any of their arguments.

I find that that the same compare game is weaseling itself back into my soul as I work with startup communities around the world. We have all seen this in the rankings of various startup communities. I too am both a victim and purveyor of this. I am sorry, I am trying to rid myself of the ploy.

One of my mantras is this: Startup communities are like children—they should never be compared.

You see, on one hand, community leaders need a way to evaluate how well they are doing. On the other hand, the same leaders get caught up in using other communities’ attributes as a marker or milestone to set up goals for their community.

I feel like I am back listening to my children again. “If Jessie got a new pair of ice skates, then I should get a new pair, too!” Never mind that her sister did not ice skate or even care that much for ice skating.

In community speak, it might sound something like this, “Columbus, Ohio has a $100M new venture fund, I should get one, too,” says every Midwest city.

I firmly believe that the source of this thinking is rooted in a very simple motivation—we don’t know how to do this, and if something works for someone else, I need to do it too. By the way, we have no idea if that action on the part of the Columbus community will do anything to help inspire more entrepreneurs or help build better companies or result in more jobs.

Startup community building is a nuanced game with a thousand small actions that hopefully conspire to create an environment where great things can happen. It’s that simple—and that complex.

Passionate about building your community? Take a much closer look at the tools, the actions, the activities that community builders are deploying, and dig in deep as to their actual efficacy. Then experiment in your own community and see what helps move your community forward.


Building a startup community in your city? Try organizing a Techstars Startup Weekend. All the other startup communities are doing it.

Evolving the Techstars Community in Washington, D.C.

Aligning the Techstars Startup Programs For “New Majority Communities”

The Techstars suite of startup programs are an amazing catalyst for startup communities. Its three core startup programs help engage people at various stages of the entrepreneur’s journey. However, sometimes the programs can fall into silos and lose the benefit of being part of a whole. So, what gives and is it critical for your city?

Stepping on the Ledge

Washington, D.C. was my formal introduction to the world of startups and entrepreneurship. In fact, Techstars Startup Weekend was one of the initial entry points. I was inspired to engage the community and give back by volunteering.

As I got more involved, I saw there were complimentary programs like Techstars Startup Week and Techstars Startup Digest, but no one on the Weekend crew had much interaction with them. So I set out to see how to get more involved because, at the time, there were too many organizers in the Weekend crew already. I had to piece the connections myself, which undermines a cohesive startup community.

Sometimes the programs can fall into silos and lose the benefit of being part of a whole.

So what did I find? There was no Startup Week, there was a Startup Digest.

Crossing the Chasm | Startup Week

One great thing about the Techstars Startup Programs is access to a regional manager to make connections and introductions. Just like they are able to serve as a connector, so too should the local community leaders.

I had to piece the connections myself, which undermines a cohesive startup community.

Startup Week was not active in the area, but someone else had reached out to them before me. At first, this felt like a setback, but in hindsight it was great because I wouldn’t have to do it alone.

After the experience, I was glad to have help. Like Marc Nager taught us with Startup Weekend, don’t go it alone. There’s only so much a person can do, but with others involved, you can do so much more, like build a startup in 54 hours!

So as Startup Week was getting organized, I began to lead some Startup Weekend programs. An idea popped in mind, “wouldn’t it be helpful to promote Startup Week to the participants of the other programs?”

Now I don’t know if anyone can relate, but a 5-day program that no one has seen or heard about before is not something incumbent leaders jump for joy about. I realized the uphill battle to get Startup Week credibility on the local stage, and leveraging the Startup Weekend network was critical.

An idea popped in mind, “wouldn’t it be helpful to promote Startup Week to the participants of the other programs?”

In hindsight, being part of the Startup Weekend crew already helped bridge the trust and collaboration gap that could have existed. Startup Week could have been left to its own devices. And let’s be clear, the Startup Weekend organizers are always willing to help, but their capacity is capped since everything we do is a labor of love; no Ferraris at the end of this tunnel.

The Uphill Battle | Startup Digest

Another great thing about Techstars is the leadership development they make available. For our purposes, every year there’s a summit for all community leaders across its startup programs to provide training and share ideas across cities.

Startup Digest in Washington, D.C. has a following of more than 5,600 subscribers.

The thought of Startup Digest resurfaced during the 2016 summit, and I wanted to learn more and get involved. And in this case, there were already two curators overseeing Washington, D.C. Now here was the tough part, how was a small time upstart like myself going to begin the conversation and build trust to get in on the team?

The regional manager made the connections and I was added to the local Startup Digest team. Success? Sort of. As with any team where someone new gets thrust upon them, it was a bit awkward at first. It took time to learn the ropes so to speak and build trust.

Surprisingly the team was already looking to move on, so I became the lead curator shortly after my entry. Here’s where things got interesting. The Startup Digest in Washington, D.C. has a following of more than 5,600 subscribers. Imaging tapping into that to help promote Startup Weekend and Startup Week?

A Helping Hand | Techstars Community

All three programs now became circles that, if in silos would continue to grind away on their own, but if they converge even to a small extent they could support and bolster each other’s efforts.

The Techstars Community concept came into play, something that Aldo Aguirre mentioned as we pushed to hold various events to co-promote the upcoming program initiatives. In fact, we surprised Aldo with a co-hosted rooftop social mixer to celebrate the various partners and entrepreneurs.

And that’s just a tip of the iceberg.

So what’s the benefit? Well after a year of struggling to align the programs where it made sense, here’s what came out so far:

Startup Weekend

  • Give: Virtual sessions during weekend program for promotion
  • Take: Promote events to program followers

Startup Week

  • Give: Right of first announcement and/or winner speaking opportunities; promote programs
  • Take: Promote events to program followers

Startup Digest

  • Give: Highlight startup/entrepreneurs in weekly emails; prize certificates
  • Take: Promote signup to program followers

Cross Functional Collaboration (all three programs)

  • Communicate sponsorship opportunities for all programs one-time during the year (instead of hitting the same organization 2–3 times across the programs)
  • Host community events that can help with outreach and engagement
  • Engage partners as Techstars Community (rather than individual programs)
  • Email newsletter coming from Techstars Community collective

And that’s just a tip of the iceberg. For 2018, the collaborations have expanded to think up a calendar of events to move each program’s needle forward.

    The Journey Continues

    Is this the direction all cities should follow? Not necessarily. It works for Washington, D.C. because in an area where the ecosystem is splintered and duplicative efforts are the norm, it just doesn’t make sense for the long game.

    As we continue to map out the Washington, D.C. ecosystem using the Startup Community Maturity Model, we need to become more collaborative to help mature the ecosystem into the next phase.

    I’m also in a unique position where I touch all three programs. This is not the norm across cities that I am aware of, so some unexpected challenges may come up. However, as we continue to ask Techstars to increase the support they provide, cross-functional collaboration is something we should consider at the local level.

    There’s only so much a person can do, but with others involved, you can do so much more, like build a startup in 54 hours!

    And as traditionally underrepresented groups become the new majority in the upcoming years, we need to be intentional about how we engage across programs and with limited resources to provide the best support for the next generation of startups and small businesses.

    This original post can be found on Meldium.

    Editions Month Spotlight: Beverage Innovation

    Whether you’re a craft brewer, coffee connoisseur, have a great idea for a new product, or the next innovator for beverage products you’re welcome to join Startup Weekend Tampa for their Beverage Edition during Editions Month, to build, launch, and startup!


    We interviewed Stasha Johnston, Digital Marketing Director at Monin; a gourmet flavouring company created in 1912 at Bourges, France, that was born because its founder started delivering orange syrups to bars and restaurants by car. Now the company focuses on premium cocktail flavours and exports to 45 countries out of Tampa, having presence in over 140 countries.

    Their innovation comes along with the statement, “You can go from ordinary to extraordinary,” which they achieve by adding to your regular beverage one of the more than 150 flavours offered in different options– syrups, sauces, purées or mixes.  

    Stasha believes that “‘beverage industry’ and ‘innovation’ are two words that have to go hand in hand, because everyone is drinking beverages, and if an entrepreneur wants to enter the industry they will need to deliver intriguing and innovative solutions for consumers to feel engaged with a specific product.”

    She says consumers are getting smarter, so companies need to have more awareness on who they are selling to, what kind of products they are creating, as well as delivering higher quality in every sense– ingredients, packaging, promotion. Her final advice for entrepreneurs joining the industry is to identify something they believe is special and move forward with the execution of the idea before the bigger companies find that trend, product, or service.

    One of the major changes happening in the industry is the shift from carbonated beverages towards the focus on healthier and organic products.

    The opportunities to reinvent the industry are everywhere; on April 1st, the Daily UK, published an article about 11 year-old Mikaila, a girl from Texas, who got an investment of $11 million from Whole Foods to sell her lemonade sweetened with honey.

    The organizing team of Tampa’s Startup Weekend Beverage Edition is partnering with some of the best in the beverage, tech, and business communities to give you all the resources and advice you’ll need to launch your business in 54 hours. You can learn more about the event below.

    What are you most excited about for your upcoming event?

    We’re excited to see Tampa’s beverage community come together for this event! We’ve got a blooming beverage community here in Tampa and I know that we’re going to have some incredible businesses emerge from this event. We’re hoping to see everything from craft brewers, to new health drinks, to beverage products, to beverage tech at this edition.

    What makes this Edition interesting?

    This event is going to be a hub for beverage startups in the US. There aren’t many places you can go to gain this kind of exposure to other beverage enthusiasts and established players in the industry so this will be the ideal place to come and launch a new beverage related company.

    Organizing team members:

    Expect a ton of free samples during our event! For more information and to purchase tickets click here.