On Deck's New Chapter: 9 Game-Changing Lessons from the Revitalized In-Person Experience

My Journey to On Deck

Never underestimate the after-taste of rejection; little did I realize then, but mine from On Deck was the driving force behind my successful journey in the tech startup world.

Back in 2018, an old housemate, fresh from an early On Deck cohort, shared stories that piqued my interest. At the time, I was fresh out of the corporate world at Accenture and had just begun to dive into the startup scene. Excitedly, I applied, but sadly, I didn't make the cut. Even though I knew they only selected a small handful from thousands of applications, it still blew my confidence.

Disappointed but not discouraged, I immersed myself in the world of startups, leading Product from Seed stage to a successful exit and co-founding Lasso in 2022. It was a rollercoaster of learning and growth. Not long after Lasso, I embarked on a new project with Alexander, where we developed an AI Ghost Editor for executive thought leadership. Everything seemed great, as we quickly validated it with $3k in pre-orders and experienced continuous growth after launch.

However, as the project evolved, Alex and I realized we had different visions for its future. We amicably chose to take separate paths. This left me at a crossroads, pondering my next move. Was this the project where I should invest my future years, and did I want to do it solo?

Seeking clarity, I ventured from Lisbon to San Francisco. A conversation with Gaurav, an On Deck alum, highlighted a key learning I had made about myself: I thrive in a team environment, realizing that collaboration, not solitude, is where my true potential unfolds. His encouragement led me to On Deck's doorstep once again.

This time, however, I was accepted into On Deck.
Initially, I planned to use the opportunity to find a co-founder; However, a conversation with my good friend Mark offered a different perspective. He advised;

“Don’t just look for a co-founder; look for people you want in your life for the next 20 years.”

This advice resonated deeply, prompting me to reframe my objectives going in. After seven days of non-stop conversations with founders, I have accumulated these insights from the cohort and the following alumni/founders*:

• Eoghan McCabe, CEO of Intercom

• Adam Spector, CEO of Levy

• Sasha Orloff, CEO of Puzzle

• Elaine Zelby, CEO of Tofu

• Julian Weisser, Co-founder at On Deck

• Anne Dwane, Partner at Village Global

• Andrew Munday, CEO of Local Kitchens, Employee #1 at DoorDash

• Peter Walker, Head of Insights at Carta

• Ansel Parikh, CEO of Finch

• Ryan Delk, CEO of Primer

• Sunil Rajaraman, CEO of Hamlet

• Matt Rastovac, CEO of Respell

Below, I share insights gathered from this experience. *These are my notes from conversations and talks that resonated with me and don’t reflect all of the opinions of the founders mentioned.

Julian Weisser from On Deck and Andrew Munday of Local Kitchens

1. The Founding Team:

• Defining Roles: Establish clear roles within your founding team, particularly regarding leadership positions like who will be CEO.

• Equity Split Realities: Despite advice advocating a 50/50 equity split, most startups display unequal splits between founders. What’s most important is that you talk about it.

• Vision and Excitement Alignment: Ensure co-founders share a vision and excitement about the idea, open to its evolution.

  • Questions that can prompt alignment discussions

    • Why do you want to build a startup?

    • Why does this market interest you?

    • How excited are you to spend the next ten years serving this audience?

    • If the initial idea were to change dramatically, how likely is this to change your interest in working together?

2. Opportunity Recognition and Validation:

• Market Gap Identification: Focus on identifying market gaps and prioritize distribution strategies.

• Practical Validation: Embrace Adam Spector’s "Rule of Ten" for real-world validation, i.e., do it ten times manually before you automate it.

• Responsive Market Adaptation: Continuously iterate based on market feedback.

3. Deep Market Analysis and Strategic Planning:

• Comprehensive Market Understanding: Dive deep into market dynamics and trends. Understand the inflection points that will enable you to win against incumbents.

• Effective Competitive Positioning: Conduct thorough competitive analysis for strategic differentiation.

• Coherent Strategy Formation: Develop a clear, actionable plan for market entry and growth.

  • The kernel of a good strategy includes

    • Diagnosis of the situation

    • Your approach to winning in the market

    • A coherent set of actions that compound to improve your position

4. Fundraising and Financial Strategy:

• Demonstrating Capital Efficiency: In this market, you need to demonstrate capital efficiency and craft a compelling value proposition.

• Crafting a Market-Relevant Narrative: Align your startup's story with current market dynamics and investor interests.

• Strategic Investor Alignment: Seek investors whose visions resonate with your startup’s goals.

• Bigger is Easier: Solving the world's most complex problems can be easier to rally support for because of the potential return it can bring to investors.

5. Execution and Team Dynamics:

• Team Alignment and Culture Fit: Assemble a team in sync with your startup’s vision and culture. Don’t hesitate to let go of people who do not fit the culture.

• Adaptable Execution Strategy: Be prepared to pivot in response to market feedback and internal assessments.

• Do the Hard Thing First: Consider models like ‘1,2,3, the Dragon’, i.e., start by solving three low-hanging fruit problems and the hardest one.

6. Scaling and Sustaining Growth:

• Achieving Milestones with Minimal Expenditure: Aim for significant achievements with minimal resource use. Keep salaries low in the early days.

• Leveraging Network Effects for Growth: Focus on building products or services that become more valuable as more people use them.

• Competitive Analysis for Sustained Advantage: Use insights from competition to maintain a competitive edge.

7. Personal Growth and Leadership Development:

• Resilient Founder's Mindset: Cultivate a mindset of learning and adaptability.

• Conviction and Self-Belief Building: Develop strong belief in your vision.

• Managing Emotional Challenges: Navigate the emotional highs and lows of entrepreneurship. Therapy, meditation, and a personal board of directors are just some ways of creating support frameworks for your life as a founder.

• Hope is a Critical Ingredient: Keeping the team motivated and hopeful about the future is as important as any business strategy.

8. Defining Entrepreneurship and Understanding Key Risks:

• Entrepreneurship Defined: Creating value from resources beyond direct control.

• Risk Assessment: Focus primarily on market risk while not overlooking execution and technology risks.

9. My Biggest Personal Takeaways:

• Overcoming Limiting Beliefs: Embrace a bold vision of the future while maintaining a healthy skepticism for the present.

• Building Conviction: Strong belief in your venture is key to persuasion and success. It is what enables you to hustle harder than anyone else.

• Leveraging Unfair Advantages: Recognize and capitalize on your unique strengths and expertise. You are an expert in more areas than you might think.

• Aggressive Solution Exploration: Push for ambitious solutions over incremental changes.

• Balancing Independence and Collaboration: Understand when to lead solo and when to harness the power of teamwork.

These insights are not just lessons; they've been transformative experiences that have reshaped my outlook on entrepreneurship. They serve as guiding principles as I continue my journey. Still, most importantly, I feel a deep sense of gratitude for the relationships I have gotten to develop from this experience.

Applications for ODF20, which kicks off 1/26, are now open. If you want to apply and have any questions, please message me. I am happy to answer them.