
Picking a (Business) Partner
If picking a business partner feels like choosing a spouse with a cap table, that’s because it basically is. Partnerships are like leverage, they can multiply your opportunities, adding incredible value if managed carefully, but can create risk if you choose poorly. According to a Harvard Business Review study, nearly half of cofounding partners end up buying one another out due to rifts and power struggles. Translation: great partnerships don’t “just happen”; they’re designed, vetted thoroughly, and maintained.
How it all began...
Ben and Jonah met playing broomball in the dead of the MN winters. Friends first, we then spent a few years “dating” to figure out if our core values aligned and we would work well together. Ben helped Jonah buy a rental property. Jonah shared with Ben his perspectives on best practices for investing at the institutional level. Slowly forming a vision for Legacy Investment Group, Ben and Jonah acquired the first two investments together to stress test the partnership before taking on the massive responsibility of having friends and family invest alongside. The following blueprint to partnership is what has shaped our success so far and laid the foundation for Legacy's future growth.
What “great” looks like
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Complementary and overlapping skills (not clones like Tom Brady’s dog). Map your strengths and look for your opposite. A classic combo is to find someone with operating experience and someone with finance and underwriting experience. This is our blueprint at Legacy Investment Group.
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Shared vision & values (alignment before everything). You need agreement on the destination and the rules of the road: what the vision is, how the business operates, who has responsibility and accountability for what, and how you communicate when things get bumpy. A shared mission is critical, as is the ability to grow and evolve.
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Trust & integrity (the real measurement of success). Partnerships work because there is trust; make sure you are working with someone you trust who has shown through their actions that they have the highest level of integrity.
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Communication (clarity beats winging it). Agree on update frequency, who owns which decisions, and how you’ll share challenges. Internal communications should be proactive and scheduled. At Legacy, we have found that in-depth quarterly and annual retreats where leadership can block 1-3 days to (re)-align on vision, brainstorm, plan and implement is critical to our growth and success.
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Work ethic & resilience (especially in the grind). Partnerships are stress-tested by missed projections and 11pm fire drills, not ribbon cuttings. The day-to-day life of an entrepreneur or small business owner is not all rainbows and sunshine; however, the flexibility and rewards can outweigh everything. Look for a partner who shows a pattern of delayed gratification and problem-solving under pressure.
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Industry knowledge (or access to it). You don’t both need 10+ years in the niche you've chosen, but together you need the full stack (deal sourcing, operations, finance, legal, capital markets, etc). Surround the core partnership with A-level team members and build an exceptional support network (attorneys, CPAs, lenders, mentors and more).
Due diligence: underwrite the person like the deal
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Reference the references. Call former colleagues, investors, lenders, and vendors. Ask for one win and one miss, then verify what “owning the miss” looked like and lessons learned. If you do not have a long history with the person, consider background checks. Reputational risk is real, and you don’t want to be surprised.
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Financial stability & incentives. You’re not judging net worth; you’re checking reliability under capital calls and stress. Make sure structures (waterfalls, fees, promotes) create alignment between you and your partner as well as with your investors.
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Chemistry with structure. Chemistry over coffee or bourbon is important; legal documents are critical. Choose the right entity and capture your understanding in writing. Make sure to address roles and responsibilities, what happens if a partner can’t meet a capital call, what requires unanimous consent vs one partner, define triggering events like death or deadlock, and what happens if things don’t go to plan. As fun as improv is, your structure is not something you want to say “yes, and” to.
Operating rhythm: how healthy partnerships stay healthy
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Run on a schedule. Figure out the appropriate cadence for reviewing important operating metrics and strategy planning. We talk informally on a daily basis, have weekly leadership meetings, bi-weekly operational reviews, monthly KPI discussions, quarterly (strategy, capital, people) and annual offsites (budget, comp, growth goals).
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Invest in the relationship. Maintain a growth mindset and be open to self-improvement. Be honest with yourself and your partner and hold your partner accountable to treat you the same with regular 1:1’s, feedback both ways, and no surprises.
In short: pick a partner for character and complementary skills, verify with diligence, hard-code alignment, and operate like adults. Do that, and your partnership becomes a force multiplier, and you will achieve much more than you ever could on your own. Cut corners on partner selection, and you’ve funded your attorney’s kid’s college education.