Blood, Sweat, and Business: The Real Pros and Cons of Working with Family

[Ashley Wilson]

Family and business: two powerful forces that shape our lives. Separately, they’re complex enough—but mix them together, and you’ve got yourself a high-stakes cocktail of loyalty, emotion, ambition, and legacy.

I should know. Over the years, I have worked and partnered with my husband, father, brother and mother, but I know I am not alone. From mom-and-pop shops to multi-million dollar family empires, partnering with loved ones can be a dream come true—or a slow-motion train wreck. The stories are legendary: siblings building global brands, spouses scaling real estate portfolios, cousins co-founding tech startups. But for every success story, there’s an equally dramatic tale of fractured relationships and bitter lawsuits.

So, is going into business with family a smart move or a ticking time bomb? Let’s break it down.

✅ The Pros: Why Working with Family Can Be a Game-Changer

1. Built-in Trust (Usually) When you're dealing with someone who’s known you since you were in diapers, or “until death do we part” there's often a deep level of trust already established. You can skip the background checks and get straight to building the business.

2. Aligned Values and Vision Families often share similar worldviews, values, and long-term goals. That alignment can be rocket fuel for a unified brand and decision-making process.

3. Loyalty That Runs Deep Family tends to stick around—through rough patches, growing pains, and pivot points. They’re more likely to weather the storm instead of jumping ship.

4. Cost Savings at the Start Many family-run ventures begin with sweat equity and a shared understanding that "we're all in this together." This can lead to more financial flexibility in the early stages.

5. Legacy Building Working with family gives you a chance to create something that outlives you. That sense of legacy can be a powerful motivator.

❌ The Cons: When Business Gets Personal

1. Emotions Can Hijack Logic Disagreements are inevitable in business—but when your CFO is also your cousin, or your partner is your spouse, a simple business dispute can turn deeply personal real fast. Often this comfort and familiarity within a relationship can be a double-edged sword.

2. Lack of Accountability Family ties can blur the lines of authority. Would you fire your underperforming brother? Would your niece take constructive feedback seriously? Accountability is needed for any business to succeed, so a lack of it can be the first sign of a business destined to fail.

3. Unclear Roles & Expectations Without clearly defined roles, responsibilities, and boundaries, the business can devolve into chaos or resentment. This is further amplified when the roles in one’s personal relationship is vastly different than the roles in the professional one.

4. Difficult Conversations Become Really Difficult You might let things slide to “keep the peace,” but avoiding tough conversations is a recipe for long-term dysfunction—both at home and in the office.

5. Fallout Can Ruin More Than the Business If things go south, you’re not just dissolving a partnership—you could be fracturing a family. Holidays get awkward, and Sunday dinners become war zones.

How to Make It Work: 5 Survival Tips for Family Businesses

1. Set Clear Boundaries: Keep personal issues out of boardroom meetings, and don’t let business bleed into every family gathering.

2. Put It in Writing: Treat it like any other business. Have operating agreements, role descriptions, compensation plans—even exit strategies.

3. Bring in an Outside Advisor: A neutral third party can help mediate disagreements and bring objectivity into emotionally charged moments.

4. Prioritize Communication: Check in regularly—not just about business, but about how each person is feeling in the partnership.

5. Plan for Succession Early: Don’t wait until a crisis hits. Decide early who takes over what, and how decisions will be made as the business evolves.

Final Word: Should You Do It?

The truth? Working with family isn’t for everyone. If your family bond is strong enough to survive the rollercoaster of entrepreneurship—and if you can balance heart with strategy—then yes, blood and business might just be your winning formula.

But if you’re not ready for some serious soul-searching (and contract signing), it might be best to keep family at the dinner table—and out of the boardroom.

Personally, it has led to the best and (occasionally) the most difficult situations in my life, but I would not change a thing!