👋 Hi my name is Roslyn, I’m a 2x founder and executive coach. I help founders fall in love with building their companies again. Learn about working 1:1 here.

Hi there,

The last couple of these newsletters have focused on the topic of co-founders: how to have a healthy relationship with your co-founder and how to heal from a co-founder breakup.

To complete the cycle (in reverse order lol), today I want to start from the beginning: how to pick your co-founder and ensure you’re a good fit before you make the very big decision of going into business together.

We’ll cover:

• Green and red flags to look for in a potential co-founder

• Discussions to have with your prospective co-founder

• Agreements to have in place should you choose to move forward

NYC female founders, we’re walking again this Friday November 7th, with a special partner this time around. Scroll down for more details and RSVP here.

By the way, there may or may not be a newsletter next week… I’ll be in Costa Rica on a yoga & meditation retreat… so if not, see you back here Nov 18th. 🌿

Where we go deep on the inner and outer work of building a startup.

How to Choose Your Co-Founder

WHY IT’S IMPORTANT

Choosing your co-founder is one of the most important decisions you’ll make in the life of your business.

This is the person you’ll spend the majority of your working hours with for the next 7–10+ years (for investor backed-businesses), or possibly longer.

They’re the person you’ll ideate with, brainstorm with, and build alongside as you take your idea from 0 to 1.

You’ll navigate the ups and downs of product-market fit, hiring, fundraising, and leadership together.

You’ll also make countless hard calls together: where to invest, who to hire or let go, and when to pivot, persevere or even shut down.

And as I talked about in the last newsletter: this person will be a mirror. They will influence not just your business success, but your sense of self-worth and wellbeing!

Yet, when we consider the magnitude of impact of this one person on our business and lives, many founders choose a co-founder without doing nearly enough due diligence. They team up because someone has complementary skills, investor connections, or industry experience, without deeply understanding who they are as a human being.

As a coach, I unfortunately often see co-founder relationships become a source of stress instead of empowerment.

So today’s newsletter is for anyone exploring potential co-founders or having early partnership conversations. And hey, it’s just as useful for existing co-founders before making big, long-term decisions like raising a round, pivoting, or building out a team.

We’ll look at four key areas:

🟢 Green flags: the qualities to look for.

🔴🟡 Red and yellow flags: areas of concern.

💬 Questions: discussions for understanding who someone really is.

📝 Agreements: structures to set you both up for success.

Keep in mind: no one will be perfect. The goal isn’t to find someone with zero red flags. It’s to understand their self-awareness, alignment and fit with YOU and whether you can grow through challenges together.

🟢 GREEN FLAGS  

Qualities that signal emotional maturity, integrity, alignment, and the capacity to navigate challenges together.

• Emotional maturity and self-awareness. They’re aware of their emotions and patterns, they can take accountability for them and have tools for working with them.

• Clear communicator. They express needs, feedback, and ideas directly and respectfully.

• Alignment and intrinsic motivation. They’re here because they care deeply about the mission, not just the potential exit or the external validation.

• Kindness and compassion. They lead with humanity and want to positively impact your team, customers and other stakeholders.

• Values alignment. They share values with you and can uphold them even when things get tough.

• Complementary strengths. You bring different strengths that create great impact when combined.

• Resourcefulness, initiative and creativity. They come up with ideas and solutions, not excuses, in the face of challenges. They take ownership and move things forward.

• They’re doing (or open to) the inner work. A willingness to reflect, heal, and grow is needed to navigate challenges and grow with the business.

• Tools for exploring inner blocks. They have ways to explore and work with limiting beliefs, unhealthy patterns, and core wounds that might be coming up through the business and/or relationship.

• Optimism balanced with realism. They can believe in a big vision while staying aware of the risks and grounded in what needs to happen day-to-day.

• Trustworthiness and transparency. They share openly, both good news and bad (and especially their own mistakes). They can come to you when they’re having a hard time and say “I’m struggling with x”.

• Growth mindset. They believe in their capacity, and responsibility, to grow and evolve as a leader. They value feedback in order to grow.

• Resilience under stress / tools for regulating. They know how to take care of themselves - mentally, physically, emotionally, and spiritually - so they have capacity to navigate difficult situations. They know how to ground themselves when things get stressful instead of spiraling or shutting down.

• Integrity and follow-through. They do what they say they’ll do, even when it’s hard or unglamorous. 

🔴🟡 RED AND YELLOW FLAGS

Behaviors or patterns that, if left unchecked, can erode trust and collaboration.

• Avoidance of conflict. Unwilling to have hard conversations, leading to resentment or passive aggression.

• Lack of follow-through. Consistently not doing what they say they’ll do.

• Speaking negatively about past collaborators. A sign of unresolved baggage or victim mentality.

• Selfishness. Consistently prioritizing self over the company or team.

• Blaming others. Avoiding accountability when things go wrong.

• Over-identifying with ego. Needing to be “the visionary”, “the face of the business” or always right.

• Poor emotional regulation. Lashing out, withdrawing, or making rash decisions under stress. Consistently relying on unhealthy coping mechanisms that impact their ability to show up (e.g. numbing through through social media, alcohol/drugs).

• Misaligned ethics. Willingness to cut corners, treat people poorly or compromise values.

• Defensiveness when given feedback. This makes it hard for them to grow as a leader, and to raise issues to them.

• Trauma bonding. Choosing someone who unconsciously mirrors an old dynamic (e.g. seeking approval to feel safe) can keep you both stuck in survival patterns.

Having one or two of these doesn’t automatically disqualify someone. (Let’s be real - you probably have some red flags too!) We are human beings, imperfect and all healing something. What you do want to look for is self-awareness and willingness to work on it.

If they can name their own patterns and take responsibility for how they show up, that’s actually a green flag in disguise.

For example, if I were having this conversation with a potential co-founder, I might say:

“I’ve historically struggled with conflict and tended to avoid hard conversations, which is a fawn response I learned earlier in life. I’ve been working on it through Parts Work, nervous system mapping and Non-Violent Communication. My commitment is to name when I’m avoiding and pause to regulate before re-engaging honestly.”

If someone can have that kind of conversation, it shows both courage and capacity for growth.

💬 QUESTIONS FOR DISCUSSION

These questions are designed to illuminate the green and red/yellow flags and help you understand how someone thinks, feels, and responds when life gets real.

• What does success look like for you, personally and professionally? This checks for alignment in vision and values.

• How do you like to make decisions? Data, analysis, intution? This clarifies whether your operating styles match or are complementary.

• How do you handle conflict or tough feedback? Shows emotional maturity and communication skills.

• What triggers you? This reveals emotional and pattern awareness and hopefully regulation tools they have or inner work they’ve done. 

• What are your zones of genius and what’s most energy draining for you? Highlights complementary strengths (and potential areas you both dislike - so you can plan accordingly).

• What motivates you? Differentiates between intrinsic motivation and external validation.

• What’s your relationship to money? What beliefs and patterns do you have around it? What role does money play in your life? Surfaces potential tension around fundraising, co-founder & team compensation, and exits.

• How long are we in this for? What are your expectations for what we’ll achieve in that time and what happens if it takes longer? Aligns on timeline and long-term commitment. Most important is the part about if it takes longer. (It almost always takes longer so definitely spend some time talking this through).

• What happens if someone wants out?  Prepares you for that scenario and helps you understand their thinking around how it could play out, what would be considered “fair”.

• What are your views on work/life balance/integration? Helps levelset expectations on pace and boundaries.

• What are your other major roles and commitments in life and how will you prioritize them? Helps understand their other priorities and how they’ll all be managed or integrated?

• What happens if someone becomes a parent? Level sets on what it looks like when priorities shift, co-founder parental leave, etc.

• What are you financial needs? Now, and in the future, what is your floor and ideal compensation?

• What values would you sacrifice to uphold (e.g. reject money from an investor or fire a top performer to uphold)? Reveals their ethical non-negotiables.

• What do you need to feel supported by a co-founder? Ensures you can show up for each other effectively.

• When have you experienced burnout before, and how did you manage it? Helps understand self-awareness around wellbeing and what triggers burnout for them.

• What are your non-negotiables in life and work? Brings clarity to what’s important to them and also surfaces potential dealbreakers.

• How do you recharge? Helps you understand their tools for rest/recharging.

• How do you respond when things don’t go to plan? Uncovers resilience and coping mechanisms.

• How do you like to give and receive feedback? Builds trust in communication.

• What’s a major mistake you’ve made in the past, and how did you take accountability? Tests integrity, honesty and ownership.

• How do you navigate uncertainty or stress? Reveals nervous system awareness and how they handle uncertainty (which there will be a lot of!).

• How do you like to manage or lead? Tests cultural and leadership compatibility.

• What’s your philosophy on leadership and team culture? On team compensation? What do you look for in hiring people?  Checks for alignment on people values.

• What quality of yours is most likely to threaten our business or relationship? Gauges humility and self-awareness.

In addition to asking these questions, check in with your body’s wisdom. Do you feel light and open or tight and withdrawn? Safe and connected or subtly on edge? Notice if you feel activated or compelled to people-please. These are signals from your nervous system and intuition.

Your nervous system catches what your brain might miss.

📝 AGREEMENTS

Even the best relationships need structure. The following agreements create clarity and prevent resentment and conflict down the road. Put these into a written agreement, co-sign it, and consider getting a lawyer’s review (especially for the parts related to equity, comp, conflict resolution and what happens if someone exits).

• Roles & responsibilities. Who owns what? What’s the scope of each person’s role, now and how do you see it evolving as the company grows? 

• Equity split.  In general, an equal split can often feel better long term in true partnerships, even if one person brings more early on. The journey is long and both people will feel more committed and empowered. (Although there can certainly be exceptions to doing it this way).

• Compensation: How will each founder be paid (or not) until profitability or funding? How does founder compensation scale with profitability/funding?

• Communication norms: How and when we’ll meet, make decisions, and check in emotionally.

• Transparency protocol: What information do we agree to share openly (financials, department key metrics, concerns, performance)? 

• Decision-making process: How will major strategic calls be made? Debate, consensus, domain authority, voting? What about when we get stuck? 

• Values & decision alignment: How will we ensure company decisions stay true to shared values when under pressure? 

• Feedback culture: How will we give and receive feedback to each other? At what cadence? Regular check-ins make hard conversations easier.

• Conflict resolution: What happens when we disagree or communication breaks down? Mediation, coach, take a pause and come back?

• Time commitment and energy: What does “full-time” actually mean? What seasons of life and business need/offer flexibility?

• Boundaries & wellbeing: What are our boundaries around work hours, communication, and time off? How do we protect rest, vacation and personal lives?

• Learning & growth: How will we support each other’s development (coaching, retreats, personal growth budgets)? How do we keep both founders evolving?

• Exit or evolution: How do we handle shifting roles if one of us outgrows or evolves beyond our initial scope? What happens if someone wants to leave? 

IN CONCLUSION

Choosing a co-founder is a major decision for your business and life. You’re choosing who you will ride the highs and lows of entrepreneurship with.

The right co-founder will challenge you, regulate with you, celebrate with you, and grow alongside you.

When you find the person who sees it this way and is ready to commit to that kind of a partnership, it can become one of the most powerful forces in entrepreneurship and also a deeply satisfying relationship in your life.

So take your time, have the important discussions, and listen to your intuition.

WITHIN WALKS

We’re hosting our next female founder walk on November 7th!

Our next Within Walk will be sponsored by Céleste, a sensual wellness company specializing in indulgent supplements that quiet the mind and open the heart, elevating the magic around us.

We'll be making Celéstial lattes together at the C Cafe before our walk, with Céleste's Élixir d'Extase.

In honor of this partnership, our walk theme is channeling our intuitive knowing as the divine feminine — in business and in life.

• ​Recall a time you followed a quiet inner knowing. What did you do, and what evidence showed it was the right call?

• ​What practices or rituals helps you hear your inner voice more clearly?

• ​Where are you still outsourcing decision-making today and what would trusting yourself look like instead?

• ​If you let your deepest feminine values lead the next phase, what would you do differently? How would it feel?

If this sounds like a conversation you’d like to be a part of, RSVP here.

• 1:1 Coaching: Want to go into 2026 feeling clear, grounded and supported? Book a free coaching consultation to learn how we can work together.

• Walk with me: Join for our next Within Walk.

• Let’s be friends: on LinkedIn and Instagram. I share more startup content and what’s going on behind the scenes there.

• Finally, tell me how you liked this newsletter. I read every piece of feedback.

Thank you for reading today!

With love,
Roslyn 💚