I'm writing this article as an extension of my reflections for recalibrating my five-year plan now that time has expired for my previous five-year plan. You can read my previous five year plan and next vision for where I want to be career-wise in the cast below:

Jack Dishman on Warpcast

After high school, my five year plan was to become a great programmer and to be able to build applications. Did that. After college, my five year plan was to become a startup founder. Kinda did that but not as a founder role, rather as an employee first-hire. I’ve learned that a startup can mean many things; could be a company with low head count that has existed for 5+ years or a VC-backed idea. Now that was 5 years ago, I have to recalibrate my goals. I have decided my next five year plan is to be a key player in an efficient business. Feels like a demotion but it doesn’t have to be. I’ve learned it takes a flexible team with balanced skillsets to accomplish that and doing it alone is lonely and improbably unrealistic. I still see myself as a glue guy and great team player, thats why I added the key player part. Efficient business means sustainably generating revenue for a product people are willing to pay for. How that plays out? We will see.

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I've been the first engineer at three startups now, where I've taken on a senior & managerial role. I know five years isn't a substantial amount of experience to some reading this article, but I'd like to recount my lessons learned and insights from working with founders and building out products from ideas for my own personal reflections.

The Founder Role

Founders who have raised capital have successfully convinced both investors and employees of their vision. They must be compelling advocates for a moonshot idea that promises to change the world. As captains of the ship, employees rely on founders for cultural direction and a sense of purpose.

One of the best attributes I’ve seen in a founder is the ability to connect with employees on a personal level. Genuine compassion beyond the role’s requirements can significantly boost employee satisfaction. A great founder is like a coach who motivates their team, balancing empathy and drive, and getting the most talent out of each player by putting them in positions to thrive. This aligns with a Gallup study that found engaged managers can boost employee retention and productivity by up to 70%. Too much "buddy-buddy" familiarity can blur work-life boundaries and undermines professionalism, while too little leaves employees feeling unrecognized.

Transparency and honesty are especially crucial in small teams. At a startup convention I attended last spring, founders debated how much financial information to share with employees. Many advocated for sharing just enough to quell concerns while withholding specifics to avoid distractions. While I understand this perspective, I believe employees are disadvantaged when layoffs come abruptly without prior insight, or can at least offer alternative perspectives in smaller teams that are oftenly a "flat" hierarchy structure.

Paul Graham recently wrote about "Founder Mode," highlighting how founders often receive advice to hire good people and step back. Brian Chesky of Airbnb found this approach nearly sank the company. Staying deeply connected to the product and team is key. I've seen the same—founders who remain engaged foster stronger cultures and avoid the pitfalls of becoming detached. Delegation matters, but losing the founder’s hands-on vision can be harmful.

Hard Lessons Learned

A key lesson I've observed from founders whose ventures didn’t succeed is that they often lose focus on the product development status and roadmap. They become so engrossed in raising the next funding round that they disconnect from the very thing they’re building. The ability to pivot when traction isn't progressing and recalibrate towards a direction with higher signal for revenue is a hard realization to make. Missing that move can lead to a slow drain of funds and time.

High turnover is a major red flag in startups, signaling dissatisfaction and likely foretelling a similar experience for future employees. Whether it’s due to unrealistic expectations or a culture of overwork, burning out employees—especially those with little equity—quickly leads to a talent drain. LinkedIn’s 2022 Global Talent Trends report showed that the average turnover rate across industries was 10.6%, with startups often experiencing higher rates, signaling dissatisfaction.

Self-burnout is just as real. I found myself working early mornings and late nights, driven by a desire to see progress. But when results didn’t meet my expectations, I felt drained. I learned to keep a healthy balance by incorporating off-screen activities, like walking my dog, throughout the day. Burnout is a significant issue, costing the global economy an estimated $1 trillion annually due to lost productivity.

The grass isn’t always greener at another startup. If you’re feeling unfulfilled and considering jumping to a higher-paying role at a new startup, think twice. Money often comes with strings attached, and gut instincts about culture and fit tend to matter more in the long run than a bigger paycheck.

In times of turbulence, having founders who maintain their composure is vital to team morale. In remote or hybrid settings, miscommunication is common, and poorly interpreted messages can easily create disruption. Most of us have witnessed “drama” in Slack or work messages, and we know how distracting it can be. From my experience, the best way to handle such situations is to address them privately, then, if necessary, publicly post a reflection on how to avoid future issues.

As a manager, having my team's back and avoiding finger-pointing when issues arise builds stronger relationships with coworkers. It goes beyond saying “we” instead of “I”—it means that when something preventable goes wrong, the entire team reflects and establishes measures to prevent repeat issues.

I still have lots to learn about startups and building successful products, so I'm hoping in my next five year reflection, I can give more advice on how to succeed, instead of pitfalls to avoid as a founder.