Help me bring 100 tech founders to 100 rural towns in America

Ann Wessing
6 min readNov 30, 2016


From my perspective, the most important outcome of the 2016 US election was the spotlight it shined on how divided our country is right now. There certainly are many problems to solve in the near term, but this divide might be the most important. This divide indicates that we cannot agree to common values as a country, and this is problematic regardless of which candidate won. Moreover, while the great divide is not soley geographic in nature, I think it is fair to say that rural America generally sits on one side of the divide while urban America sits on the other. Neither is right or wrong, but we cannot win as a country if we fail to understand each other.

Given the importance of fixing this problem, I’ve been searching for ways to bridge the divide. I thought about making a donation to different organizations. I even thought about running for office. While these ideas were good starting points, none seemed to address what is most fundamentally needed: exposing each side to the other to promote dialogue and to help us find commonalities instead of differences. Then, after visiting my hometown in rural Wisconsin for Thanksgiving, I realized something — the stories of our modern-day entrepreneurial founders can bring our country together while spurring innovation. Moreover, this initiative will allow rural Americans and urban tech professionals to gain much needed exposure to each other. For that reason, I’m on a quest to bring 100 tech founders (ideally diverse founders) to 100 rural communities across the country in Q1 2017. Here’s why and here’s how you can help:

Why exposure to both sides is important

While many have stated that their echo chamber pre- and post-election was one-sided, my experience has been different. I straddle two very different worlds: my pro-Trump, rural Wisconsin hometown of 1,1oo largely blue collar folks and my pro-Clinton Stanford-educated social circle of San Francisco tech professionals. These two worlds — both of which I care deeply about — filled my echo chamber with a healthy mix of support for both candidates. I didn’t realize my unique and fortunate position until after the election when many people commented about being “in a bubble,” feeling completely blindsided that there could be such divergent thinking in their midst.

What I’ve learned about those in my hometown is that many recognize Trump as imperfect, however, they are willing to put aside his imperfections for the sheer hope that he may drive meaningful change for them. When I probed on Trump’s unequal treatment of minorities, individuals in my hometown admitted they see the unequal treatment happening, but they are not very concerned about it. I believe their lack of concern is caused by their lack of exposure to these populations. Its hard for rural white Americans to care about minority groups when they do not know someone directly who is being impacted.

Similarly, when I discussed Trump’s election with friends in Silicon Valley, many admitted they do not know a single person who voted for him. One entrepreneurial friend, a woman interested in fixing massive problems in this world like many in Silicon Valley, stated, “this is an America I do not know.” I responded with, “if you want to fix real problems, this is an America you must make an effort to get to know.” For example, she would benefit from seeing how hard working rural Americans are — many work multiple jobs, seven days a week, for minimum wage. They do not have retirement accounts. They do not have paid vacation time. In many cases, they do not have exposure to education programs to build their skill set. Again, its hard to have empathy for rural America when you do not know someone in that neck of the of the woods.

I thought a lot about these two groups over the last few weeks: struggling rural Americans trying to keep up in a changing world and Silicon Valley tech leaders trying to change the world as quickly as possible. Despite their different goals, I realized one thing both have in common is the value placed on hard work and their interest in making America great. These were commonalities we could build upon.

Then, it hit me in the middle of the night. Instead of talking about politics, where the wounds are still raw, what if the two sides could engage in dialogue and mutual support on innovation in America? These conversations could expose Silicon Valley to the “real America” that hasn’t yet used Uber, Slack, Airbnb or Dropbox. Imagine the innovation that could be sparked and propelled by introducing Silicon Valley to some of the hardest working men and women in rural America and the realities of the noble lives they lead. Moreover, these conversations could also expose rural America to tech entrepreneurship, the future of our country, and perhaps high-contributing diverse founders who represent groups rural Americans haven’t been exposed to. Imagine the cultural influence of connecting rural America to some of the most successful female, African American, LGBTQ, immigrant and Muslim entrepreneurs within tech. I think this exposure would allow each of us to hear and understand more from the opposing echo chamber while also increasing our sensitivity to the other side.

How you can join in

With that, I have set a goal to facilitate 100 conversations between tech entrepreneurs and rural Americans in Q1 2017. I’m calling the program “Starting Up America,” a title that refers to not only sharing how start-ups are transforming America, but also to the act of charting a new, more growth-oriented course in America. This new course being one of open dialogue where we seek to understand each other more. Perhaps this effort can shape future elections, but more importantly, perhaps it will do a small part in saving the most important American values: equality, mutual respect and entrepreneurial innovation.

The Starting Up America program will take place in small towns across the country, places that rarely have out-of-town speakers. Each live event will feature at least one tech founder’s story — their background, how they overcame struggles to launch their company, and their vision for tech in our country. Most likely, their struggles will not be all that different from the struggles of the audience. And, rural Americans will be encouraged to share their concerns about tech and what they need to drive innovation and entrepreneurship in their own communities. Politics won’t be a planned topic, but if political issues surface, healthy dialogue won’t be stopped. Conversation is the key element of what will be a very informal program — my guess is that these conversations will take place in the local diner, donut shop or high school gymnasium. (Update: I am even exploring a partnership with a national high school business club to involve the next generation of entrepreneurs in this endeavor.)

To make this happen, I am looking to match tech founders with “hometown hosts.” I need 100 of each. The hometown hosts ideally are people like me — someone who grew up in rural America, but who has been exposed to tech and diversity. Ideally, the hometown host is still positively connected to his or her small town such that he or she can promote the program and manage event planning logistics.

So, how can you help?

  1. Volunteer to be a hometown host here.
  2. Volunteer to speak as a tech founder here. (We’d especially love women, people of color, immigrants, Muslims or LGBTQ to share their story!)
  3. Financially contribute to this effort here. Funds will go towards founder and host travel expenses as well as event promotion.
  4. Spread the word by sharing this post in your networks and on social media.

All of us are incredibly motivated to drive change and all of us are looking for ways to help. All of us want to drive innovation to change the world for the better. Moreover, many of us want to understand “the other side.” This is one way, and I hope you will join in.



Ann Wessing

Small town girl with big dreams.