Day in the Life of a Founder: A Journey of Mastery and Gratitude

Dwayne King

It’s a funny title right? Every day is so radically different from the last at an early-stage startup, it’d be impossible to pin down what you do. If someone asked me, ‘What did you do today?,’ I’d have to go look at my calendar, emails, and Slack messages to reconstruct my day. A friend said it well, ‘Ah, you’re in Blursday.’ And Blursday it is. That said, if there’s a common thread across each day, it’s gaining competency in my drive towards mastery in skills I had little or no competency in before founding a startup. And, looking around, while it doesn’t always feel like it, realizing just how fortunate I am to be doing what I’m doing. To that end, each day for me is a quest towards mastery, with a feeling of deep gratitude.


  1. Sprinting a Marathon: As I embark on the Rutabaga adventure, it’s official – I’m a serial entrepreneur. Having founded and scaled a consultancy before, I thought I knew what to expect. But a SaaS startup is a different beast. In the consultancy, growth and team scaling went hand in hand with increased revenue. In contrast, a startup demands an all-hands-on-deck approach from day one. It’s less wading into the waters and more diving headfirst into the deep end. This stark contrast has been both a challenge and an exhilarating learning curve.
  2. Wearing Multiple Hats: As a founder, I’ve quickly learned that versatility isn’t just valuable – it’s essential. Each day brings new roles and responsibilities, many of which were initially outside my comfort zone. Embracing these roles has been a pivotal part of my journey, helping me grow both as a leader and a professional.
  3. The Fundraising Challenge: Fundraising is a realm where I’ve felt particularly out of depth. Yet, the progress I’ve made over the past few months is astonishing. The strides in competency are a source of personal pride and motivation.
  4. Developing a Thick Skin: The startup landscape is an emotional rollercoaster. One moment, potential customers are visibly excited about Rutabaga, and THEY’RE ASKING YOU, “What are our next steps?” The next moment, a VC dismisses your hard work or tells you you’re too early – or too late – for their portfolio. Navigating these highs and lows has been an exercise in resilience and mental fortitude.


  1. Co-founders’ Votes of Confidence: My co-founders’ decision to join me in this venture, leaving behind stable, high-paying jobs, fills me with immense gratitude. Their faith in Rutabaga and in me as a leader is something I cherish deeply.
  2. Dedicated Team: The commitment of our team, many of whom are working for little or no pay, is incredibly humbling. Their belief in Rutabaga’s vision and their trust in my leadership continue to inspire me every day.
  3. Angel Investors’ Confidence: I am immensely grateful to our angel investors. Their ability to see Rutabaga’s transformative potential and their belief in us as the right team to bring this vision to life is incredibly affirming. Obviously, we believe we’re the right team with the right vision, but the third-party validation of investors reinforces this confidence.
  4. Fulfilling Work: Despite the exhaustion, the joy and fulfillment I derive from my work are immeasurable. Launching and growing a meaningful business with a team I deeply respect is a rare and precious opportunity. I am profoundly grateful for every challenging, rewarding day.

Every day in the life of a founder is a blend of mastering new skills and appreciating the journey. It’s about growing, learning, facing challenges head-on, and being thankful for the opportunity to do so.

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