6 things I notice about successful modern startup founders

Chris Cunningham
In the Trenches with C2V
4 min readFeb 6, 2017

I have been part of the startup ecosystem for a long time. Initially as a founder and later as an executive, advisor and investor. My personal startup journey has taken me to technology markets and business cultures around the world. Each step of the way, I’ve tried to take notice of what the successful people around me were doing.

Though every industry, region and culture have their own unique characteristics, I have developed a set of traits common to the people and companies I’ve watched become successful over the years. When I step back and examine those traits, it’s clear what I am really looking at are a series of small behaviors that add up to create the opportunity for founder success.

What follows are my 6 observations on successful startup founders today.

They fly under the radar

It’s easy to fall into the classic startup trap of pursuing the spotlight too much. But messaging every financing round with a PR roadshow, or each product feature with a marcomm blitz, can seriously shorten runway for a startup. One thing I notice about successful modern startup execs is their willingness to fly under the radar both as a company and as a founder. One of the companies in my C2 portfolio, ZenRez, is killing it as a consumer play despite having spent very little on PR or marketing in their first 18 months. That strategy has let ZenRez sneak up on more well-established rivals and wrest away market share. Whether it’s born of humility, strategy or budget restriction, keeping one’s head down and mouth shut in the early stages of a startup can be smart.

Their technical chops are improving

Many companies that I find myself intrigued by today have a technical founder on the team, often in a CTO or product management role. This is so different than just a few years ago when a couple suits with sales skills seemed to front every startup. The approach then was to fund business people and let them hire the tech talent. Today we’ve learned that good companies often have that visionary founding tech leader as part of their winning formula. I’d be very interested to look at data that correlates success (breakeven, profit, exit) for startups that have technical cofounders versus those that don’t. A tech savvy founder signals to me that a startup’s product plan and business plan are coordinated and aligned.

They’re on-time and focused

North American professionals are often a little late to meetings and calls. It’s a bad habit we’ve developed. The routine here is to hold the meeting up and make small talk until everyone arrives. This would never happen in Germany, for example, where a premium is placed on the team’s time. Meetings start exactly when they’re supposed to start, they address exactly what’s on the agenda, and you need to be there. If you’re not, the team isn’t waiting. This rule is the same whether you’re the CEO or the most junior staffer. In my time working with Unacast and my Norwegian peers I’ve had to push myself to match this strict commitment to schedule and task. I have to say, I’ve come to really respect it. Test this at your startup and see how it changes behavior.

They know their numbers

Predictable, recurring revenue that can be forecasted month over month is the best way to build a stable business and improve margins. For many of the startups I deal with going with anything other than SaaS or DaaS monetization would be suicide. So, getting to a financial model happens early-on, partly because there’s established tools for market validation. A lot of the exceptional founders I see these days are gifted analysts. They’ve mastered the art of analyzing the data surrounding their business to identify new value propositions for consumers, their clients and industry. In taking these messages to market, today’s founders are getting very good at explaining and validating nascent market opportunities — a key step for every startup.

They communicate consistently

Good founders never make you ask for an update. They communicate with team, partners and investors routinely. They demonstrate this trait in all phases of the startup. Early-on, consistent communication builds trust with investors who want regular updates on business health, cashflow, new hires, or challenges faced. Good communications habits are are also valuable for making sure board members have the data they need to provide strategic guidance. Market address, employee engagement, technical roadmap . . . in every phase of the organization, clear, regular communication adds value. Today’s successful founders are all over this.

They are diversified

A week or so ago, I had breakfast with a prominent NYC investor who told me that he thinks every CEO of the companies he invests in should sit on boards of other startups in unrelated fields, simply as a means to observe and learn for their own business. I couldn’t agree more. As someone leading business at a data startup, who also invests and advises a number of companies, I have learned the power of a global perspective. Successful startup founders don’t wear blinders. They study other industries and verticals and expose themselves to ideas and activities that challenge their perceptions, both professional and personal. This agility of mind and breadth of skills is perhaps the most consistent characteristic I see in today’s successful startup founders, wherever I may go.

Chris Cunningham is Chief Revenue Officer of Unacast, founder of C2 Ventures, and a Limited Partner with Bowery Capital and Techstars.

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