Milwaukee’s Dance with Entrepreneurial Trust

Over the last couple months, my mind has been sifting how Milwaukee can most effectively broaden its entrepreneurial ecosystem. It is what you do when building a business at the heart of that community.

Industry vanguards have shared their templates on the important elements of this work. The entrepreneurial bible on this process is Startup Communities by Brad Feld. There is much to learn from his experiences in Boulder, Colorado and what he describes as the “The Boulder Thesis”. However, each community finds itself at different stages of development. Each city’s building process is positioned at varying points in the economic cycle. And each ecosystem has different cultural values that make them unique. Understanding these nuances and adjusting the playbook to most effectively leverage the individual richness of different parts of the country is essential to success. For Milwaukee, this will be no different.

The Influence of Trust

One of the core pillars of the Boulder Thesis is the idea of an increase in connections – the idea of engagement and sharing of broad entrepreneurial experiences and knowledge, primarily among startup entrepreneurs, but overall across all stakeholders. By creating forums and venues in which this kinetic interaction can occur, you raise the tide of knowledge and build stronger relationships within the community. We have seen some measures to do this in Wisconsin. For example, Tom Still and the Wisconsin Tech Council have more broadly attempted to engage with all of the state’s communities, holding meetings in areas they historically have not targeted.

This broad relationship building and outreach must be a long-term process and strikes at one of the key elements of successful entrepreneurial systems – creating trust amongst its stakeholders. When we think of what trust means, how it is built – it is formed by a combination of time and action. One earns trust through a consistent and persistent exchange with another individual. Family is the most vivid example of trust – relationships and exchanges that collide over generations, day-in-day-out interactions that weave the bonded fabrics of life and human chemistry.

The Cyclicality of Trust

So why is trust so critical in an entrepreneurial community? Given the uncertainty of young businesses and their entrepreneurial leaders, given the uncertainty of the day to day events within these businesses and efforts, given the propensity for high failure rates and associated financial risk embedded in those outcomes, the stress and heightened emotional exchanges that naturally occur as a result of these conditions tear at the connective tissue that holds relationships and communities together. Only through strong trust can a community weather such forces and the “normal” every day storms of entrepreneurship.

Milwaukee finds itself sitting like other cities at the tail end of economic cycle, but different from others, in that it has arrived at the venture/entrepreneurial cycle late. Wisconsin, in particular Milwaukee, will in all likelihood be building its entrepreneurial ecosystem in the midst of an economic downturn. Thus, the stress that naturally accompanies during such periods for startup businesses will exert additional pressure and potentially dislodge much of the progress that ecosystem leaders have created and/or are creating. Only through a persistent trust in one another can we hold the ground that we have achieved thus far through the likely turbulence ahead.

Building the Entrepreneurial Community Inside-Out

Recently, I had the chance to attend a MKEtech quarterly meeting at which IT leaders from around the greater Milwaukee area convened to discuss the work and results from the last couple of years. They also outlined their plans and goals for the future (MKEtech Meeting – Deck).

One of the ideas discussed was to frame Milwaukee to corporate businesses from around the country as a regional port of technology commerce. In addition, there was much talk about tethering out to the coasts and other mature entrepreneurial cities to leverage their experiences and knowledge. Broadly, these types of efforts could be characterized as an import strategy in ecosystem building.

While beneficial and part of the long-term plan given how communications and technology is bringing cities and people closer together, these types of efforts seem premature as the focus given where Milwaukee is from a development perspective. Priority should be kept on building the foundation locally – organic resource and talent formation, education, and support. We have yet to achieve a density in which our resources, whether they be entrepreneurs, corporate, academic, or investor, can be split and extended broadly.

Additionally, other cities around the country are competing to tie into these core entrepreneurial hubs. Our efforts do not exist in a vacuum and while the flag of “Collaboration” is waved high in the air as a sounding cry of innovation, competition for attention and seats at the table will always remain.

If we were to see a slowdown, the natural retrenchment towards core relationships and strongholds of trust will occur nationally and in Wisconsin. If we wish to utilize our resources and time most effectively, an import strategy should be pursued in times when society feels confident and more open to new relationships. The door to extended relationship building never completely closes but does swing through the ups and downs of cycles. Paying attention to its position as a means to optimize our growth will be essential.

Bringing it Home

Bold Coast Capital has the motto of “Our Home, Our Journey”. Given the current geographic focus of the firm, the natural interpretation of this phrase aligns well and could be assumed. However, “Our Home” has a deeper meaning and tie. I believe Wisconsin’s defining trait is its steadfast embrace of family and midwestern values and there is no better representation of that culture than a home. Our entrepreneurial system should be built and tied to this unique and defining trait.

Wisconsin has a rich tradition of multi-generational family-owned businesses and it is imperative that these centers of influence and wealth around the state embrace the entrepreneurial movement for the broader community to succeed, especially in the city of Milwaukee. These families have built their foundations through relying on one another, by building TRUST within their tight circles of association. Only by extending this trust, opening themselves up to a broader spectrum of the upstart business community will the ecosystem garner strong traction and see the types of growth being witnessed in other parts of the community.

I believe Milwaukee business leaders can become more open and trusting. I believe the same types of family values and culture that have been the pillars of legacy organizations and family-power brokers can be shared and woven into the identity of our entrepreneurial community. I believe we are at an inflection point and look forward to the bright prospects of our entrepreneurial home!

Recommending Readings/Perspectives:

Startup Communities – Author: Brad Feld
Valley of Genius – Author: Adam Fischer
TechStars podcast – Speakers: Brad Feld, Chris Heivly, Eric Reich (March 6, 2019) – Deck Presentation (March 7, 2019)