The majority of entrepreneurs lean on friends and family for their first capital infusion, and yet few take the time to think through the potential pitfalls of those investments. Founders have moral and fiduciary obligations toward those friends and family members, especially if they’re not experienced investors. And they must be thoughtful about how to involve them without risking important relationships.
We talked to founders who have gone through the ups and downs of running a business and have managed to do right by their friends and family. Following their advice will help ensure your earliest investors know what they’re getting into—and make it likely you’ll keep getting invited to their holiday dinners, regardless of whether your business thrives or fails.
—Lewis Hower
As Joshua Greenough began opening up about his idea for a startup (a coupons app called Bankons) friends and family got excited. Some, including his mother-in-law, offered to invest.
Grateful as he was for her support, he hesitated. “As a founder, you have a moral obligation,” Greenough says. “What happens if the business fails? Does the person really understand the risk involved?” After pondering those questions, he got back to his mother-in-law – “I said no.”
“What happens if the business fails? Does the person really understand the risk involved?”
After pondering those questions, he got back to his mother-in-law – “I said no.”
Greenough, however, said yes to others in his inner circle, including his father, a finance executive with more than 20 years of experience. His father clearly understood the investment risk. What’s more, he stood to benefit, albeit intangibly, even if Greenough’s startup failed. “His bet on accelerating my own career was his own downside protection,” Greenough says.
Not every entrepreneur has a veteran CFO at the ready, but Greenough’s experience offers powerful lessons for anyone seeking to raise startup funds from friends and family.
The lessons are especially important, given the outsized role friends and family investments play in the startup ecosystem. A 2014 survey by the Kauffman Foundation showed that 40 percent of startup funding came from friends, family and business acquaintances. In all, friends and family contribute tens of billions per year to new ventures, and the average individual investment is $23,000, according to crowdfunding site Fundable.
Be clear about the risk
Given that, it’s no surprise that many entrepreneurs take friends and family investments for granted. But mixing money and personal relationships can be risky, especially when things go south. If you want to preserve relationships no matter how your company ultimately does, your number one responsibility is to be candid about the risks.
“Mixing money and personal relationships can be risky”
“The one thing I stress the most is that the downside is zero dollars,” says Sarp Sekeroglu, CEO and co-founder of Water Pigeon, echoing Greenough and scores of other founders. “If you’re relying on this money for anything important, do not make this investment in me or anybody else.”
Indeed, ending up with zero dollars is not the exception, but the norm. One in five startups fail in its first year and a half fail by their fifth year, according to the Bureau of Labor Statistics.
Of course, entrepreneurs start companies because they believe in themselves and their ideas. Their optimism can be contagious. So after clarifying the risks, picking the right fundraising strategy and making sure any transactions are properly documented, what else do you need to think about?
The pitch
There are some ways to craft a pitch tailored to family and friends. A close relative might appreciate hearing about your idea face-to-face, whereas a former colleague that you’ve kept in touch with over the years might be okay with an email. (Check out our Bonus Checklist below for some conversation tips.)
Danny Harris, a founder who recently launched mobile app GMDY, emailed about 40 people. Most were close friends; some were family and colleagues. And all had some familiarity with his idea for a sportswear shopping app. “There was no secret with the group that I was reaching out to,” Harris says.
He could have benefited from more personal outreach. “It’s easy to ignore emails”
While Harris was able to raise the money he needed, he says he could have benefited from more personal outreach. “It’s easy to ignore emails,” he says.
Details, details, details
After you’ve gotten some interest, a major question that comes up is how much you should disclose? The answer depends on who you’re talking to.
For someone who is unfamiliar with business and startups, keep it at a high level. Greenough recommends you describe the opportunity, discuss timelines and the milestones you hope to achieve and maybe talk about the size of the team you plan to build.
Going into the financial nitty-gritty is probably not necessary. “Unit economics and total addressable market are not relevant to the conversation because there’s no judgment and expertise around that,” he says.
“For a savvier investor or business operator, consider sharing a more detailed game plan”
For a savvier investor or business operator, consider sharing a more detailed game plan. “I would lay out the goal for the year and three years,” says Sekeroglu. Here, you might want to discuss specific metrics, like the number of units you expect to sell or the profit margin you’re targeting, just as if you were pitching a professional investor, he says. And like with any pitch, do not overpromise, he adds.
Managing involvement
Once you’ve raised a family and friends round, managing expectations can be tricky. Some family members and friends may overstep and feel their investment gives them a say in business matters. Others may think it’s okay to pester you with updates.
Greenough recommends being clear with investors that they will all get periodic updates at the same time, perhaps monthly or quarterly. “Just build that habit,” he says. (Here are tips on what to include in those updates.) While he still had to field investor calls from time to time, the regular updates kept everyone on the same page.
What’s more, they helped to foster a team spirit around his startup, as friends and family cheered whenever he reported milestone or win. “It felt like (they wanted) to be in the arena and in the journey with you, to celebrate those wins,” says Greenough.
Don’t turn friends and family into a crutch
If your business starts gaining traction, it may be tempting to lean on your friends and family even more. And why not? They too may be starting to taste success, so why should you deny them more potential upside?
As tempting as that may be, it’s a crutch you should avoid. Your startup will likely do better over time if you go through the disciplined assessment required when pitching professional investors.
“Too many cash infusions from friends and family are likely to make your cap table unwieldy”
What’s more, too many cash infusions from friends and family are likely to make your cap table unwieldy, which may turn off future investors. “That’s one downside of too many friends and family investments,” says Sekeroglu.
Experience pays off
Finally, if you have friends and family who can add value besides money, consider it a huge asset and don’t be afraid to lean on it. Greenough realized this firsthand when his business was on the verge of going bust, and being able to tap his father’s experience proved to be a lifeline. He reached out to him, and over a dinner, made three points. “I need your experience,” he recalls. “I need to give you an investor update. And I need you to be my dad.”
Knowing Greenough had built something of value, his father pushed him to get a $50,000 bridge investment. That proved to be enough to keep the company afloat until he was able to sell it.
All his investors ultimately ended up with a modest gain, which given the company’s brush with failure, was pretty good. “We were about to go to zero,” he says. “So yes, they were happy with the outcome.”
There’s a lesson there too. Your investors don’t want any surprises. Be transparent with your friends and family and keep them in the loop about your ups and downs. It should help smooth things over especially if you hit a rough patch or worse.
Bonus Checklist: Share this with your friends and family
Before you dig into the details with your friends and family, share this checklist with them first.1. One in five startups fail in their first year, and half fail by their fifth year. If my company fails, your investment could go to zero.
2. Invest only if you can afford to lose this money. If you need it for anything important, please walk away.
3. If you are interested, I will tell you more about my vision, goals and milestones, and be candid about the challenges I’m likely to face.
4. If you decide to invest, I plan to update you on our progress, along with all other investors, via email on a regular basis. You should feel free to get in touch if you have additional questions, but be mindful that I’ll be working around the clock trying to build a successful business.
5. If you have relevant expertise, I will be grateful for your for advice. But your investment won’t give you a say into how I run the company.
6. Your support means the world to me, and I will work as hard as I can to succeed and deliver a good outcome to all my investors.
If you found this article helpful, please check out our Startup Insights for more advice around cap tables, dilution, and finding angel investors.