The classic "difficult" entrepreneur personality could be your startup's greatest strength.
To "drop in" is to catch the wave - to have the right of way and to show everyone else in the lineup what you've got. We're rooting for you. We've invited some of the best storytellers we know to share their style with us. Enjoy the drop in.
Startup founders are a national treasure - they’ve created that particular style of American entrepreneurism behind the moonshot ideas and biggest technical innovations of the last decade. At the same time, startup founders are SO FRUSTRATING. Anyone who has worked with a founder has a list of those moments that made us want to quit or commit a felony. Why can’t they just get it together? Stay focused? Show up on time?
The thing with founders is that they’re required. You have to take the good with the bad. If you can’t figure out how to work effectively with them, it’s you who won’t be around for long - they’ll be fine. I’ve worked with founders for 13+ years in startup roles in Silicon Valley and now run my own brand strategy company working with even more founders across the B2B landscape. Maybe I need my head checked, or maybe I’ve just figured a few things out. Either way, I’ve found that understanding how to effectively work alongside different founders has played a crucial role in my work and in my ability to help my clients succeed.
Why Founders Work This Way
If you’re good at following directions, can stay focused on a task and work well with others - you’re probably enjoying a lucrative career at Deloitte. If not, you might be a founder. Entrepreneurs are designed this way for a reason. Let’s take a quick look at some of the common personality traits of founders and tactics for making the most of their quirks.
This fundamental founder trait is what makes entrepreneurs so fun to watch. They’re always thinking about the big picture, always five years into the future - which can be annoying when you just need sign-off on that presentation that was due two weeks ago. The reality is that it’s often easier for founders to think about flying cars than this quarter’s hiring plan.
How to work with Futurists? It can help to “sell” the present day to future-thinking
founders. Emphasize the company’s current opportunities and momentum in
conversations - it’s not that you’re ignoring the big picture; instead, the steps you take today help get you closer to achieving that vision. These founders are great for media work - get them in front of a camera and make sure they’re trained on talking points that start with the present day – while also leaving room for 2025.
From early explorers like Ferdinand Magellan to present-day founders like Jeff Bezos, no boundary can contain the expansionists. These founders have a hard time saying no and tend to jump into new ideas and new business ventures quickly. Getting bored easily drives these founders to always be on the hunt for the next big thing - often what they were reading about at 2:00 am.
How to work with Expansionists? You might pair these founders with an excited
advisory board of industry experts who can help both practically vet new ideas and soundboard ways to expand within the company’s current focus. Put these founders’ energy to work brainstorming ideas for projects you want to see done in the company. Reverse psychology can be a useful tool here, too. These founders do well with opportunities to speak at events and roundtables with people from other sectors.
Unlike the expansionist, this kind of founder is laser-focused on one part of the business – the one where they have the most experience and skill themselves (commonly sales or technology in Silicon Valley). The result is a founder who is disinterested or frustrated with other elements of building the company. Unfortunately, it’s often the part of the business that the founder feels personally strongest about that gets dysfunctional in the startup as it grows.
How to work with the Cyclops? Delegation can be easier with this kind of founder for projects outside their core focus. Taking a strong right-hand advisor role can help the founder understand their blind spots. Do try to expand their focus a bit by translating other work into language that lines up with their area of focus. In media, this kind of founder’s personal passion can be a gold-mine for trade press, byline content and speaking events. Put that passion to work!
Being a founder is mind-blowingly stressful. Some founders juggle it better than others. This type of founder is likely to have 10 hours of meetings scheduled at 15 minute increments every day and never, ever shows up on time. They think that they’re super busy and productive, but really are at risk for burnout and being spread way too thin. Behind this trait is a layer of anxiety about needing to do everything personally or risking having it all fall apart.
How to work with the Overwhelmed? Sometimes, it helps to proactively pry work out of this kind of founder’s stressed-out hands. See if you can anticipate what they need without asking. For example, this founder may appreciate your producing a package of photos and bios to help prep for an upcoming event or sending a recap before the return to the office after a day away. It’s more work for you, but the ROI is major. Strongly consider schedule constraints before making this kind of founder your primary spokesperson.
A more elusive founder type - for a reason. These founders avoid talking about the company, want to keep things in “stealth mode,” and feel uncomfortable in the limelight. They take an “if we build it, they will come” approach to the business. Sometimes, it’s because they don’t value/understand marketing (see: The Cyclops). Often, it has to do with elements of embarrassment and fear.
How to work with Shadows? It’s really hard to make a founder into a pitch-master if they don’t want it at their core. Best case, they’re open to having someone else in the company be the public cheerleader. Worst case, you need to figure out a plan that smartly turns a “quiet” brand into “mysteriously alluring.” If they lean toward a Cyclops trait, see if you can’t develop one area of focus where they’re comfortable getting out there. As I tell my founder clients, the only way you get to stop talking about your company is if it goes out of business.
Becoming a Founder Aikido Master
Whether your founder fits perfectly into one of these traits or is a mix of a couple different aspects, you probably have your hands full at the office. One of the most important things to remember when working with any kind of founder is realizing that it’s not about you. Like Aikido in martial arts, succeeding with founders is about taking that person’s energy and redirecting it through you to get what you need to succeed. Knowing your own strengths and anxieties is a huge advantage when thinking about how to best collaborate with founders.
At the end of the day, I love working with founders because they’re never boring, they’re full of big ideas, and they bring so much energy to the company. Learning how to make the most of your company’s founder can be one of your greatest professional advantages. Leverage the good traits, navigate the quirks, and help your startup rocket to the moon.
Emily Peters is founder of Uncommon Bold - a San Francisco-based brand strategy studio for startups. She has 13+ years experience working alongside startup founders, especially in the finance and health technology sectors. Emily has spoken on the topic of startup culture at VentureBeat, the Ministry of Awesome, PLAY and SXSW.