Don’t be a Dickwad Founder

Danielle Gillespie
5 min readApr 26, 2022

A borderline rant. For founders and people thinking about joining startups.

I work with a lot of startup founders and continue to do so because, in general, the experience has been very rewarding. However I was talking to a colleague the other day about surfing the fine line between giving the appropriate advice to a founder or giving the advice that the founder wants to hear. Sometimes, when you give the appropriate advice, the job concludes quickly because it may not be input that the CEO was expecting. On the other hand, if you give the advice that is desired, you might preserve the job but at what price?

I recently posed the question on Twitter, as a result of one of my recent engagements. Full disclosure: my Twitter account is probably almost as lame as it can be without being dead but I do get some impressions and occasionally somebody engages. So, minor victories. I tweeted, “I would rather lose a contract for giving good advice than keep the contract alive by spoon feeding a CEO what he/she wants to hear.” One person responded that most of his clients want to pay him for what they want to hear, rationalizing that the client will ultimately fail on their own. Hmm? It seems like the kind of person paying to hear what they want to hear would also be the kind of person not willing to accept blame for a mislead strategy.

The post was inspired by a founder I recently worked with who most certainly did not want anyone on the team ruminating on any original thoughts. So here is a list of things to do if you don’t want to be a dickwad founder (note that the term ‘dickwad’ is gender-neutral in this writer’s humble opinion):

1) Lead Analytically, not Emotionally

Do you want to be fed your own rhetoric or do you want genuine insights, no matter how difficult they may be to accept? Less than 10% of your decision making process should be affected by emotions; in other words your gut feeling or rules of thumb can get you into a ballpark but 90% of your decision making process should be led by fact-based evidence.

As major decisions arise, founders should take the time to reflect on their potential choices to determine whether they are satisfying an emotional need or a business objective. All good founders have deep empathy for the problem they are trying to solve but great founders can identify and understand when there is evidence pointing them in a new direction. A founder’s empathy is the spark that got the ball rolling for their startup idea but, the analytical part of the the brain needs to take over in order to hit the gas.

As a founder, if you find that you are in a place where you have a deep desire to fulfill an emotional need (and it’s ok to be honest with yourself), you should consider building a lifestyle business rather than a business that is expected to reach massive scale. Many lifestyle businesses can be very profitable, enjoyable places to work that provide tremendous value and incredible professional opportunity. But, when a founder is building a lifestyle business, the team cannot be relentlessly driven to deliver hockey stick growth; the different approaches needed for the two different kinds of business will be at odds with each other and will create a hostile work environment.

Pick the kind of business you are building and understand the related fundamental approach to growth.

2) Be a Leader, not a Manager

Being the founder/CEO of a startup can be overwhelming, which means that it is especially important to be able to stay focused on the high-level vision. One way to stay on track is to establish a leadership team that can execute without day-to-day micromanagement. Even a young startup company should strive to build a team that consists of people who have expertise in different areas to ensure the business will thrive.

Great leaders:

  • clearly articulate the product mission and what makes the product/company unique
  • establish and uphold a statement of core values
  • allow the leadership team to make day-to-day decisions in support of the mission and objectives
  • do not force the leadership team to make decisions by committee, each leader has the authority and responsibility to act in accordance with the mission and objectives
  • do not undermine their teams

If you constantly feel overwhelmed or like you’re drinking from a fire hose, you’re probably managing versus leading.

It’s a fine line between allowing a team to execute according to a clearly communicated mission, where the CEO only gets involved for big decisions, and feeling it is necessary to have a hand in every single decision made by the team. Leaders of healthy organizations are able to count on their teams not only to advance the mission of the company but also to provide the details needed to do everything from creating a pitch deck, determining budget, understanding product direction, hiring new people and evaluating marketing efforts.

3) Be Coachable

Truly great founders understand that they may not have all the tools they need for success. This isn’t a commentary on the founder’s potential, intelligence or abilities. It’s simply an admission that being a founder is really demanding and it is unlikely that one person has all the skills needed for success. In my experience, founders who are not coachable and think they have all of the answers rarely succeed and seldom create nurturing work environments.

Find a coach or an accountability partner. Founders are expected to have all the answers and need to confidently set priorities and make decisions. It’s good to have an external, unbiased person to shine a different light on the challenges. Meet with your coach on a regular basis, talk through the week’s accomplishments and shortcomings, get help setting priorities, honestly evaluate performance and celebrate the victories.

Trust me, it works. I still miss the hours I spent with my coach when I was working on CorkGuru.

Founder, Founding Team Member or Employee

Even if you’re not a founder but instead, maybe you’re thinking of joining a startup company; you may be interested in identifying a bad founder before you jump in the boat. Looking for the characteristics of a good founder will likely set you up for longer term success. Great leadership starts with the founder and trickles down through the entire company. If core values are established early on, the culture will continue to be one that attracts top talent.

I would challenge you to name a dickwad founder who achieved great long-term success.

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Danielle Gillespie

Defining the intersection between technology and human connection (I also help entrepreneurs build rock solid tech products: daniellegillespie.net)