Entrepreneurs / Guest posts

You’ll wanna try this startup’s brand of entrepreneurial therapy

RedOwl Analytics cofounder Renny McPherson explains why, in its early days, the startup hired a journalist to interview its leadership team.

Joe Flood (left) and Renny McPherson, who run the podcast Numbers & Narrative. (Courtesy photo)
This is a guest post by RedOwl Analytics cofounder Renny McPherson.

In the early days of running RedOwl Analytics, we took an uncommon approach.
In 2013, we took the time to have management team members sit down and be interviewed by a freelance journalist on a quarterly basis. That journalist, Joe Flood, then transcribed the conversations and gave them back to the interviewees, letting executives decide for themselves how they wanted to build on their own words and bring up opportunities and challenges with others in the company. Only Joe, who was part of each conversation, had access to the transcribed conversations.
Why did we take time out of the day of a CEO, CTO and VP of Engineering to answer questions from a journalist?
We hypothesized that during the early phase of our startup — with each person wearing multiple hats while we found our product market fit and started to scale the business, we needed to take time out of the busy days and weeks to step back to allow ourselves more time to think broadly about the direction of the company.
We were right. Allowing company leaders and managers at our high growth startup, including myself, to take the time to be storytellers and reflect allowed us to do many things, among them:

1. Keep our eyes on the prize

Company leaders initially had a touch of healthy skepticism about whether or not this practice would add value, but we got over it when we saw results. We became very interested in stepping back from the fray and looking back and forward on goals, schedules, plans and initiatives.
The quarterly pace meant that interviews were spaced out enough that Joe could follow up on goals beyond the daily and weekly tactical ones, by holding people accountable to 100-day goals. Yet interviews were frequent enough to allow the C-suite to refocus on lost goals and to remember the best parts of the current strategy and path.
Given all the near-term business opportunities, product work, client needs and fires to put out, this pace truly tested whether each person was living up to our broader strategic vision.

2. Talk to an outsider as a form of professional therapy

By regularly talking to someone outside the company and recording the words on paper, startup leaders can see where being frustrated with someone months ago might have been one’s own fault, how relationships and working situations change and evolve. While some of the team would joke — maybe half-joke — that these sessions were good therapy, reviewing interview notes from the prior quarter was a much-needed exercise due to the high stress and long hours at a startup. Being able to admit to an outsider that certain things weren’t such a big deal seen three months later helped each person work better with their teammates.

3. Allow room for “rough drafts”

The initial germs of an idea might take a while to come together. Talking out loud to someone who listens without an agenda, allowed each person to check back on whether their passing good ideas were worthy of bringing up to the group. By the same token, by talking through things they had been thinking about at the company saying the words out loud to an unbiased third party, each person was forced to see priorities from a neutral perspective, examine their own strategy and take some of their own personal concerns out of the equation.


Allowing room for this uncommon approach was one element that made RedOwl a success today. Now under the leadership of a tremendous team that has expertise in all functions of a business, with a staff of more than 60, the Federal Hill-based company continues on its mission and vision to secure the human layer of the enterprise. With backing from several investors and a $17 million Series B fundraise in 2015, I believe the company is well set up to continue to be one of Baltimore’s leading startup lights.
As for me, I left RedOwl in 2015 and teamed up with Joe, the journalist who interviewed RedOwl’s leadership team. The power of that narrative and interview-based approach made us look for other examples of people talking candidly about the challenges and opportunities of a startup in real-time. We created our podcast, Numbers & Narrative, to serve as a platform for such conversations. It features local entrepreneurs like Allovue’s Jess Gartner and Pegged’s Myra Norton. (Jess shared recently that her head of recruiting and HR told her that many recent candidates said part of the reason they wanted to work at Allovue was listening to Jess’s passion, intelligence and transparency on the Numbers & Narrative podcast.)
We then took 16 of those interviews and turned them into a book to help aspiring founders and startup employees understand what it’s actually like in the early days of a company. It’s called Entrepreneurs in the Midst: Stories from Founders, Creators, and Builders.
Most people know that CEOs need to be able to tell compelling stories to sell, to raise money and to inspire a team. Taking a narrative approach with all members of a leadership team can make certain that each person is confident in his or her voice. For tech startups that rely greatly on quantitative information, this is only more necessary to create a better chance for success.

Companies: Pegged Software / Allovue / RedOwl Analytics

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