Five Business-Building Insights from the Rise of the Rest Fund’s CEO Summit

Anna Mason
Revolution
Published in
5 min readOct 11, 2018

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As venture investors, we are trained to be hyper-aware of the high velocity environment in which we live. All around us, technology is speeding up. Industry landscapes are shifting in real-time. We can plug in from anywhere, digitally interact with anyone, and track and analyze more data than ever before. But, one of the great ironies of our digitally super-connected era is that it gives us all air cover to connect less in person. However, in-person connections are often where the magic happens for startups and investors alike: insights and experiences are shared, the building blocks for formidable partnerships are formed, and people can just get to know each other.

Creating space for in-person connections has long been at the center of our Rise of the Rest place-based philosophy and investment thesis. In a continuing effort to help shift the venture capital funding geographic imbalance in our country, since 2014 our team has traveled to 38 cities to meet entrepreneurs where they are. Our Rise of the Rest bus tours have created a space where we can hear these entrepreneurs’ stories, experience their innovations, and understand the heartbeat of their cities firsthand.

This years’-long shared experience has helped to foster an interconnected web of relationships that support our investment efforts with our $150 Million Rise of the Rest Seed Fund. Now that a new community exists within Rise of the Rest — comprised of the nearly 100 startups we have already invested in from across 50+ cities in the US — we were equally compelled to bring everyone together in person for the inaugural Rise of the Rest CEO Summit.

During 1.5 days of programming last month, we presented a series of mainstage exchanges, interactive experiences and tactical workshops that could help our founders continue to build and ultimately scale great businesses all across the country.

These five insights from the Summit stood out as critical business building advice that entrepreneurs all across the country can apply:

1. Embrace Your Company’s Story to Build Value

Google Ventures’s Shernaz Daver reviewed the place of story-telling in human history: “Our history is an oral narration of stories. Our biology does not change but our stories do.” Every startup story sits at the intersection of technology and art. While founders need to focus in on the “tech” — or the hard numbers, metrics and KPIs — necessary to build a business, they also need to build a story around the company’s “art” — which is the creation of a product or service that people really care about.

2. Value Team and Culture Above Everything

Some of our founders spent time with Scott Dorsey, the founding Chairman & CEO of ExactTarget (acquired by Salesforce for $2.7B) and a Managing Partner at venture studio High Alpha. In his discussion on tactics to help take companies from “$100 Million to $1 Billion” Scott emphasized the importance of team and culture. One of his concrete recommendations was to hire a VP of People early on in a company’s lifecycle. This executive reports directly to the CEO and undertakes a lot more than perfunctory HR tasks. A VP of People gives the CEO a partner in the management of his or her growing team and increases executive bandwidth to focus on strategic business decisions.

3. Have a Clear Idea of How You Will Win

Former Alphabet Executive Chairman Eric Schmidt reminded us that every successful founder must have a very clear idea of how he or she will win. When working with early stage startups, Eric runs an exercise where he says “Give me the pitch; I am your first customer.” He has found that that can be a hard conversation because many founders have a product but they have not fully thought through their pitch and the value proposition path to acquiring that very first customer.

4. Recognize Inflection Points as You Grow

Quicken Loans Founder & Chairman Dan Gilbert has run a multi-billion dollar business empire for decades, and has invested in over 100 companies along the way. Dan explained the different skills startup executives need for different stages of growth, describing it as trying to “dock a sailboat versus a yacht,” and the frustration that can ensue when early stage traction and successes start to stall out. A critical inflection point is what Dan calls the “twenty-four hour time.” This is the period when the speed of the game is so fast and there is so much to do that a founder could easily work around the clock. Instead, this phase of growth calls for process, where a startup founder can find ways to leverage his or her time, focus on critical decisions and rely on advice and insights from others who have been there before.

5. Leverage — and Help Create — Network Density

Steve Case closed the Summit with a call to action to both seek out and support regional networks, to help create the type of community-driven density that has historically helped Silicon Valley entrepreneurs scale. “The real value is the networks. We do recognize that in most parts of the country it is harder to be an entrepreneur. It is always hard to be an entrepreneur. A lot of people are skeptical. A lot of people are fearful. When you hear a pitch, most people focus on why it won’t work. You need to focus on why it will work. And surround yourself with other optimists who embrace fearlessness and a sense of possibility.”

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Investment Partner & Human CRM at Revolution’s Rise of the Rest Seed Fund