Questions Potential Business Partners Should Ask Themselves

You and a friend have a can’t-miss idea for a new business. You’ve got a great name, and the logo is perfect.

It is time to ask each other some hard questions.

Talking up front about tough subjects like how you work, how you deal with stress and your expectations for the business can save lots of headaches later. “Most issues are neutral when you discuss them ahead of time,” says Jane Brodsky , who ran a barre-and-spin studio with a partner for 10 years in Washington, D.C. “But in the heat of the moment, issues become personal and larger than they need to be.”

Here are crucial questions that should be settled at the start to help make the partnership succeed.

How did your family communicate?

Maybe you were raised in a family that talked through disagreements to find solutions. But maybe your partner grew up in a house where the loudest voice won. That could be a problem when issues arise in the business: Experts say that when people are under stress, they often fall back on behaviours that were imprinted at home—and different styles could clash.

At Happy Being, a company that sells nutritionally enhanced teas and drink powders, the three co-founders discussed communication style before they started the business.

“We discovered that one partner gets triggered if he feels no one is listening,” says co-founder Dutch Buckley . “It goes back to an early fear of not being heard.”

(For his part, co-founder Josemaria Silvestrini says that early on he “definitely needed the validation of being recognised and being right.”)

So, the three work at making sure everyone has a say in meetings, and they made a rule that no one’s work is ever belittled. On the flip side, when someone on the team accomplishes something, someone else on the team draws attention to it.

What does success look like to you? And failure?

While these may seem obvious—like, the business either succeeds or fails—everyone’s definition is different, and they are surprisingly specific. Certainly, monetary goals or anything that can be enumerated will help partners envision each other’s goals. Is one looking to grow slowly with customers and suppliers in the community and get to better than break even after three years, while the other wants to be cash-flow positive in year one and scale quickly to sell the business to a larger entity after 10 years? There’s a lot of success and failure in between those two outcomes, depending on your perspective.

Silvestrini of Happy Being recommends hashing it out together on the whiteboard until everyone agrees on an explicit definition of success for the company. “Hopefully, it’s an easy 10-minute conversation,” he says. “Because if founders have different objectives, the boat is going nowhere.”

What does everyone bring to the table?

It is crucial to discuss what each partner is contributing to the partnership in terms of expertise, experience, network and money. Kathryn Zambetti , an executive coach specializing in founder relationships, recommends taking an honest strengths-and-weaknesses inventory of yourself and your partner and then discussing what you both bring to the table. The exercise will help delineate which responsibilities naturally suit each partner, and it will highlight areas that will require additional work or outsourcing.

The clearer the roles can be defined, the better. If you are opening a bakery, you and your partner shouldn’t both be good at just making bread. Someone needs to handle marketing, suppliers, leases and licensing, financials and hiring and managing employees.

Why are you doing this?

You and your partner need to be in complete alignment on your motivations. Does this venture need to support your family or merely add to your vacation fund? Are you doing it to prove your father or your high-school econ teacher wrong? Any answer other than unfailing commitment to the mission or the product is a red flag.

“Your north star has to be something bigger than money to succeed,” says Buckley. “People will go through things that test them, but if money is the only motive, that won’t be enough.”

What pushes your buttons?

Just like in a marriage, you want to know best how to support and protect your business partner. Understanding what puts each of you in a fight-or-flight mode can be key to getting the best out of each other.

Do you need to be consulted on all decisions, or just major ones? Do you need to be recognized as the leader and sit at the head of the table? Do you fear having to downsize your home if the business fails?

What does your workday look like?

Does a day at the office mean working 9 to 5? Can the work be done remotely and on your own time? If you work well at night and need rapid responses to questions, is it a problem having a partner whose phone goes on “do not disturb” every evening at 7? Having the conversation and understanding expectations is key.

When Buckley started Happy Being, the team learned that one of the partners got up very early. “I had to tell him, ‘We don’t want 6 a.m. calls.’ ”

Do you like taking gambles?

A penchant for lottery tickets, Las Vegas gambling or high-adrenaline activities like skydiving shows a potential partner’s tolerance for risk and whether that aligns with your own. There will be countless decisions early on in a business concerning risk, and the partners need to be on the same page.

So ask about it. You go into the venture planning and hoping for success, but how much money or time is your partner willing to lose if it doesn’t succeed? How much of their parents’ or in-laws’ money would they bet on the partnership?

Is the business more important than the friendship?

Many business partners start as friends. But would you each be willing to give priority to making the right decision for the business, even if it means possibly hurting the friendship? Would you each be capable of letting the other one go if it was better for the company? Most advisers recommend choosing a partner who has a common business goal and letting the friendship build from that, rather than trying to build a partnership on top of a strong friendship.

“Your business partner will be one of your most intense relationships, but it shouldn’t fulfill every role in your life,” says Amy Jurkowitz, entrepreneur and co-founder of branding adviser Bread Ventures. “You need to be compatible in how much energy you will both put into the business.”

If the partnership doesn’t work out, how will it end?

A co-founder relationship is a binding agreement with financial and emotional repercussions, just like a marriage. But starting a business has the added stress of having the company—the baby—arrive on day one. If there is a divorce, who gets custody?

The more specific you can be about potential breakups, the better. If you are both putting capital in at the start, would you expect to get that out if you exited? What if, several years in, one partner can’t continue to struggle without a regular paycheck and leaves—and the next year the company finally turns a profit or is bought by another company? Would the partner who left get a share of the money?

These discussions should help make it clear that the survival of the company—and not the partnership or the friendship—is the ultimate goal. Those who have been through a business breakup recommend involving a third party to help sort through these issues at the outset.

Happy is the family whose members—parents, grandparents and grown children—trust each other enough to cooperate on shared goals, especially financial ones. When that is truly the case, Uncle Sam’s tax rules can help as well.

This matters especially now that mortgage rates are above 7%, and many families are looking for ways to help younger members. If the elders have resources and are confident younger ones can cooperate, a family loan could make homeownership possible while providing the elders with a useful income stream.

Other strategies can actually lower taxes, such as when funding 529 plans or Roth IRAs, or when someone inherits a traditional IRA with required withdrawals larger than they will need.

Here are three strategies useful for functional families.

Intrafamily loans

It is perfectly legal for families to lend money to a relative for a down payment or even a private mortgage.

But it is important not to cut corners, says Ryan McKeown, a CPA with Modern Wealth Enhancement in Minnesota. If the loan is for a down payment, be honest with the mortgage provider and have a formal agreement. The lender owes tax on the interest payments received.

If the loan is for a private mortgage, both sides should have legal representation with a formal written agreement, including payment terms. The lender owes tax on the interest, and the borrower often can deduct it if he or she itemizes.

To avoid IRS trouble, the interest rate shouldn’t be lower than the agency’s Applicable Federal Rate at the time of the loan. Currently that is about 5% for loans longer than nine years; about 4.5% for loans three to nine years; and about 4% for loans three years or less. Currently, traditional mortgage rates are generally above 7%.

In addition, the lender could use the $19,000 annual gift-tax exemption (described below) to forgive some or all of the interest or principal annually. If both lenders and borrowers are married, that is up to $76,000 a year. There is no tax for the borrower on such forgiveness, because it is from a gift.

If you’re going this route, McKeown advises against having a fixed plan to forgive the debt. Instead, do it in one-off letters specifying the amount—and keep careful records. Otherwise the IRS might try to treat the loan as a taxable gift.

Asset gifts

Powerful tax-saving moves for families often use gift-tax provisions. Under current law, anyone can give anyone else up to $19,000 of assets annually, free of gift tax. That means a married couple with three grandchildren could give them a total of $114,000 in 2026.

The gifts can be cash or other assets, like stock. For noncash gifts, the cost basis—which is the starting point for measuring taxable gain after a sale—“carries over” to the recipient. So if someone buys $1,000 of stock and gives it away when it is worth $5,000, the recipient’s cost basis is $1,000. If the recipient later sells the shares for $8,000, the taxable gain is $7,000.

Here’s an example showing how gifts could save a family taxes. Grandma is a widow of modest means, while her child and spouse have prospered. The couple has two children, and they want to contribute $5,000 to a 529 college-savings plan for each—but they need to sell stock to do it. Their tax rate on the sale would be 18.8%, and they would need to sell about $11,000 of stock.

However, Grandma’s federal tax rate on the stock sale is 0%. If the couple gives $10,000 of shares to Grandma, she could sell them, pay no tax, and fund the grandchildren’s 529 plans. This saves about $1,000 of tax.

These moves are legal, and they could be used in other ways, such as to help a young person fund a Roth IRA.

But trust among family members is essential: Under the law, givers can’t put conditions on a gift. Grandma could use her stock proceeds to take a cruise, but she makes 529 contributions instead.

Mark Sellner, a retired tax attorney and CPA living in Sarasota, Fla., uses this strategy. His children sell stock he gives them and fund 529 plans for his grandchildren.

The family’s tax savings aren’t huge, but he likes other benefits. The sales by his children don’t boost his adjusted gross income, which in turn could raise his Medicare Irmaa premiums or his 3.8% surtax on net investment income.

Sellner doesn’t worry about his children using the funds for another purpose.

“There can’t be any strings attached to gifts. Of course, it is up to us to decide whether to make them in the future,” he says.

Two caveats: The “kiddie tax” applies to most children under age 24, and it is levied at the parents’ rate on investment income above $2,700 in 2026. Consider this before making gifts to a young person.

Investors who give away stock also forgo the step-up, an important provision that exempts assets held at death from capital-gains tax.

Sellner knows he’s losing a step-up, but says, “The children could use a little more now. Why should they wait 20 years to get it?”

Disclaimers

A disclaimer is a highly useful strategy in which one heir renounces an inheritance in favor of another heir. Assuming family members cooperate, this can save taxes.

Here’s one example. Dad died and had a large traditional IRA that he left to Mom. She has enough assets and income to cover her expenses, and she lives in a state with a stiff estate tax. The inherited IRA would put her estate over the threshold.

Also surviving are three young-adult children. If Mom disclaims all or part of Dad’s IRA within nine months of his death, that amount could go directly to the children. They will have 10 years to empty the account, and the family as a whole will likely save estate and income taxes.

Disclaimers have many key details, especially regarding beneficiary documents. Although heirs have great freedom in choosing what assets to disclaim, the rules about who gets disclaimed property are rigid. It is best if the original owner names tiers of heirs so that if one disclaims, the next recipient is clear.