Choosing to quit your job and go “all in” on a new idea that’s never been attempted before is a big risk. Having started two companies–ŷhat (acquired by Alteryx) and Thoropass–I can tell you first-hand that leaving a steady job w/ a paycheck for the unknown of starting a brand new company from zero can be scary.
But building “the company of your dreams” or “the company you would want to work for,” creating “the product you’d want to use” or solving “your most frustrating problem in the perfect way” is equally the most marvelous opportunity and the biggest responsibility.
This career path is a very fulfilling line of work…personally, it’s all I’m cut out for. I have often contemplated whether I’d even be employable in any other capacity if I wanted 😅!!
Don’t go it alone: how to choose the right cofounder
Having the right business partner or cofounder can make all the difference when it comes to overcoming self-doubts and building up your internal sense of conviction and confidence if you’re thinking about taking the plunge into a new venture. The startup journey will be filled with many challenges and (hopefully) many triumphs too. But the journey requires more than just your singular vision.
Startups demand the shared commitment and sacrifice of many, many people, starting with you and your cofounder(s)
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Below is a set of what i hope are practical questions one should ask oneself before jumping into a new venture with a potential cofounder…here goes:
Questions when choosing cofounders
🔍 Do I respect this person’s skills & expertise? Are they complementary to my own?
Consider if one of you is more extroverted, skilled in pitching investors or engaging with customers, while the other might excel in technology or possess unique domain expertise necessary for your startup. This synergy can fuel innovation and effective problem-solving.
🤝 Can I imagine us being able to effectively divide and conquer?
Division of labor is key in a startup. Evaluate if you and your potential cofounder can split duties and focus areas without conflict. This involves not just complementary skills, but also a shared understanding and respect for each other’s roles and contributions, ensuring a smooth and efficient leadership dynamic.
💡 Do we share the same vision and values for the company’s future?
Alignment on the company’s vision and core values is non-negotiable. Having a unified direction and set of principles helps navigate challenges and make coherent decisions. This shared foundation is essential for maintaining momentum and cohesion through the ups and downs of startup life.
🚀 When I think about working w/ this person every day, do I get excited and energized?
Your cofounder should be someone whose company you enjoy and who motivates you. The thought of working together should energize you, as this person will be your closest ally in the challenging journey of building a startup.
🧐 Does this person know how to be introspective and honest with him/herself?
A cofounder’s ability to reflect and be honest about their strengths and weaknesses is crucial. This self-awareness ensures that both of you can openly discuss improvements and changes without defensiveness, fostering a healthy, productive working relationship.
💌 When this person gives me sincere and well-intentioned feedback, do I feel grateful and motivated? Or do I feel something else?
The way you react to feedback from your potential cofounder can reveal a lot about the potential for your partnership. It’s important that feedback feels constructive and is received with gratitude, as this is indicative of a positive, growth-oriented relationship.
😤Does this person have the capacity to persevere hardships?
Does this person have a level of personal determination well above average? Have they achieved something that impresses you greatly…something that you think you would struggle to have achieved had you been in their position at the time?
💪 Does this person see and understand my strengths in a way that makes me feel pumped up and confident?
In a way, this one is almost the reverse of the one above. Another framing could be something like “does this person admire and appreciate me and my abilities and prior experiences in a way that pumps me up?” A cofounder who recognizes and values your strengths can significantly boost your confidence and morale, and that translates to better odds for success together. Mutual appreciation is key.
🌞 Is at least one of us especially optimistic when confronted with a great setback or a great disappointment?
Optimism in the face of adversity is a valuable trait in the startup world. Evaluate if at least one of you can maintain a positive outlook during tough times, as this resilience can be a driving force in overcoming obstacles.
⏳ Are our work habits and commitment levels compatible?
Compatibility in work habits and dedication is essential for ensuring that both cofounders are aligned in their commitment to the startup. It’s important to be on the same page regarding the time, energy, and resources you’re both willing to invest.
✅ Does this person check the moral and ethical boxes that matter? Can I trust this person with money and my personal reputation?
Trust is foundational in any cofounder relationship. Ensure that your potential cofounder shares your ethical standards and that you can trust them with the financial and reputational aspects of your startup.
🎚 Do I feel that we can maintain a balanced relationship, where both of us feel heard and valued?
A balanced relationship where both cofounders feel respected and valued is crucial for a healthy partnership. This balance fosters open communication and mutual respect, which are essential for collaboration and conflict resolution.
🌱 Is this person someone I can learn from and grow with over the long term?
Choosing a cofounder with whom you can learn and grow is vital for personal and professional development. Look for someone who challenges you and helps you evolve, as this will contribute to the longevity and success of your partnership.
💰 When I think about “success,” does my definition align with this person’s?
Ensuring that you and your potential cofounder have a shared definition of success is important for aligning your efforts and expectations. Differences in what success means can lead to conflicts and misaligned priorities.
🔖 Is this person willing to sacrifice the same time, money, energy, etc. as I am?
Shared commitment and willingness to sacrifice are key to navigating the challenges of a startup. Confirm that your potential cofounder is prepared to invest equally in the venture, as this shared commitment forms the basis of a strong partnership.
The Secretary Problem Applied
Choosing the right cofounder mirrors the Secretary Problem in computer science, a mathematical challenge where you must pick the best option from a series, deciding on each candidate immediately after meeting them. The dilemma lies in not knowing if future candidates might be better than those you’ve already seen.
What’s the Solution?
The optimal solution to the Secretary Problem (known as the 37% rule) suggests that you should pass on the first 37% of potential cofounders in order to gain information and set a benchmark for what the overall candidate pool looks like. Then, following the first 37%, you ought to choose the next one who surpasses all others that you have already met.
Ignoring for a moment that mathematicians and computer scientists are still debating whether this stopping strategy is actually the optimal approach, we can impute some tactics inspired by this strategy to the question of choosing the right cofounder(s).
This rule encourages us to meet and evaluate multiple candidates before making a choice. This process helps in understanding the qualities and strengths of potential cofounders, ensuring a better match for your startup and not rushing into things.
Remember, however, founding a company goes beyond any algorithm. It’s a deeply personal choice, requiring mutual respect, shared values, and a common vision. While the Secretary Problem offers a structured approach, the ultimate decision should reflect the unique dynamics and needs of your startup. Treat potential cofounders as equals, fostering a partnership built on understanding and respect, not merely as candidates to be assessed.
Be Thoughtful. Don’t Rush. Be Human.
It’s crucial to maintain a human approach, though. Yes, there are some great principles you can derive from the Secretary Problem to help you be thoughtful in choosing cofounders. But by no means am I suggesting that anyone should fully embrace the 37% rule or any purely mathematical approach to this process!.
Remember, the goal is to find someone you respect, who complements your strengths, shares your vision, and with whom you can build a successful and fulfilling business. Let the Secretary Problem guide your process, but let your intuition, respect for each other’s capabilities, and shared aspirations make the final call
Thank you to my cofounders
I have been wildly lucky to have partnered with the best cofounders on two companies. Greg Lamp , Sam Li , and Eva Pittas , partnering with each of you has provided rewards beyond measure. Appreciate you guys ❤️🙏
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Thanks for reading !! If you found this post useful, you might also enjoy these:
- Why “WHY YOU SHOULD NOT JOIN Y COMBINATOR” indicates small-minded thinking
- Lessons from ‘Failure’ in Startups
- Compliance Maze: Choose Quality Over Convenience
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