Toni Ko thought she was on top of her company's finances. Then she woke up one morning in 2016 to find half a million pairs of extra sunglasses staring her in the face.

The founder and CEO of Los Angeles sunglasses company Perverse was by then an experienced--and successful--entrepreneur, having sold her previous company, NYX Cosmetics, to L'Oréal in 2014 for an estimated $400 million-plus. So Ko was not new to managing cash flow and inventory--and she thought she was pretty savvy about finances. Despite this, in Perverse's early days Ko found herself making a very common mistake: buying more product than she could sell.

"I completely forgot my own advice," admits Ko, 44. "With my first business, the inventory was a slow buildup over the years, so I never felt cash-strapped. But as I started my second business, I overpurchased."

Ultimately, she had to trash more than 250,000 pairs of glasses. She wasn't able to recoup the purchase price--but at least she saved tens of thousands of dollars in monthly storage fees. Ko swore that next time, she would remember her own advice. "As entrepreneurs, we know a lot and learn a lot--but sometimes we forget," she says. "And this was a crucial one for me."

As Ko has now learned twice over, money is at the root of every decision you make as a business owner. But saving and spending habits are often formed--or forgotten--long before you decide how much to pay your first employee. The salary you take for a new job will determine how much money you can set aside to start your first business. The looming sense of dread you feel when you can't pay off a credit card bill at the end of the month could later remind you not to take on too much debt at your company.

To help guide you through the money trade­offs you face every day, Inc. asked founders, investors, and other business leaders to pass along the best piece of financial advice they've ever received. Some of these experts, like Goldie­Blox founder Debbie Sterling, are still building their first businesses; others, like Ko and cosmetics mogul Bobbi Brown, negotiated big-ticket sales of the companies they founded. And some, including founder Sheila Lirio Marcelo and Max Levchin of PayPal and now Affirm, have successfully navigated IPOs.

These entrepreneurs credit mentors, investors, the framers of the Constitution, and, like Ko, painfully lived personal experiences for their financial wisdom. But it's often parental wisdom that ends up meaning the most. Just ask Shark Tank investor and Fubu founder Daymond John, whose mom took him to get his first credit card when he was 18--while warning him to never fall behind on payments because "the world is built on a credit system."

Ben Chestnut, meanwhile, grew up watching his mother and sister run a beauty salon out of the family's kitchen--and learned never to spend more than the cash he had on hand.

"My mother used to tell me, 'You are the only person you can depend on to put food in your mouth,' " the 42-year-old co-founder and CEO of MailChimp recalls. "So in the early days of MailChimp, it never occurred to me to borrow money or get funding to grow my business."

Sixteen years later, his Atlanta-based email marketing firm earned annual revenue of $403 million. "If I need to make more money," Chestnut says, "I find a way to serve more customers--just like my mother taught me."

Dollars & Sense

Read below for more hard-earned advice from founders, investors, and other money experts.

 inline image

Angela Benton, founder and CEO of NewME Accelerator

NewME focuses on women- and minority-owned startups

"Make money before you start asking for it. The best way to validate your market is to get customers."

Glover Quin, Safety for the Detroit Lions

Quin lived on about 30 percent of his take-home pay during the first three years of his NFL career

"I'm going into my ninth year in the NFL and we are just now moving into our dream house. That's the difference between rich people who keep their money and rich people who lose their money: They both have nice things--houses, cars, the luxury lifestyle--but the ones who are able to keep their money live the luxury lifestyle last, while the ones who lose their money live the luxe life first."

 inline image

Debbie Sterling, founder and CEO of GoldieBlox

A STEM toy company geared toward girls

"My then-boyfriend and now-husband told me the only way to give my startup a real chance to succeed would be to focus on it full time. I saved as much money as I could, so that I had enough in the bank to last me an entire year, and put all of my attention into GoldieBlox. Nine months later, I launched a Kickstarter campaign and raised more than $250,000--and I was finally able to give myself my first paycheck as GoldieBlox's CEO."


Bobbi Brown, author and founder of Bobbi Brown Cosmetics

"When I was just starting my career in New York, my father told me, 'Don't waste your time trying to stick to a budget. Figure out how to make more money. And always spend money on good food.' "

​Zach Perret, co-founder and CEO of financial startup Plaid

"My dad told me that keeping my personal spending low would give me more flexibility than I ever imagined in my career. We spent a long time bootstrapping in the early days, and having a low burn rate was very important."

Fran Dunaway, co-founder and CEO of women's clothing company TomboyX

"Raising money is hard! You get told 'No, no, no, no' so many times--but you just have to keep at it and not give up."

Joe Fernandez, co-founder of social analytics startup Klout

Klout reportedly sold to Lithium Technologies for $200 million. Fernandez is also co-founder and CEO of miscellaneous-equipment-rental startup Joymode

"What made Klout hard was that we raised money at too high a valuation. I'd heard about not focusing too much on high valuation, and I thought, 'That's not going to happen to me.' But after our first two rounds, the final round was at $200 million. It was a pressure cooker--that was so high a valuation that the return our investors needed was really intense."

Max Levchin, PayPal co-founder and CEO of retail lending startup Affirm

"When I was going to school in Chicago, I got one of these old-school department store cards--and went from getting 10 percent off on jeans to owing more than $500 and getting calls from collectors. Ultimately, I was able to pay it off, but I felt guilty throughout--and I learned that something that's too good to be true is never a possibility in the real world."

 inline image

Jessica Mah, co-founder and CEO of accounting software company inDinero

"When inDinero ran out of funding and I had to lay off our staff several years ago, I learned to never read or believe your own headlines, good or bad. I got drunk off our press, and we grew and spent accordingly. Big mistake!"


Mark Cuban, Shark Tank investor and owner of the Dallas Mavericks

"From my dad: Don't use credit cards."

Martellus Bennett, Tight End for the Green Bay Packers and founder of media startup The Imagination Agency

"Invest in the people who help bring your dreams to life--financially and emotionally."

 inline image

Daymond John, Shark Tank investor and Fubu founder

"When I was 22 years old, a guy who owned a little bodega in my neighborhood told me, 'If you really want to start a company, you better dig under your couch for a couple of extra dollars, stop going out to dinner four times a month, trade in your car for a cheaper one, and raise that $40,000 or $30,000, if you can, by yourself.' "

Neal Gottlieb, founder and CEO of Three Twins Ice Cream

"My mother showed me how valuable each and every dollar was by working as much as she could, by clipping coupons, and by stocking up on groceries when they were buy-one, get-one-free. She passed on this sense of thrift to me--and, sure, a friend still makes fun of
me for refusing to spend $15 on a roller coaster ride back in 2001, but that helped me save up $70,000 by age 28 to start my business."

Steph Korey, co-founder and CEO of travel goods startup Away

"Rent for our first office was $6,000 per month--and we didn't have revenue yet!
We had only five people at the time, but we furnished it to fit 14, and we sublet the extra desks for $500 per month each."

 inline image

Whitney Beatty, founder and CEO of Apothecarry Brands

Apothecarry Brands designs marijuana-storage containers. Beatty is a former television development executive at Warner Bros.

"I'm in the middle of raising money, and it's easy to feel you have to be hat in hand doing whatever song and dance is needed to get an investor to invest. But the managing director of my accelerator, Jack Scatizzi, told me in no uncertain terms that
not all money is good money, and to not underestimate my value."

Alexa von Tobel, founder and CEO of LearnVest

LearnVest, a financial planning website, sold to Northwestern Mutual for a reported $250 million

"My mom taught me: Not having a financial plan is a plan--it's just a really bad one!"

Sheila Lirio Marcelo, founder, chairwoman, and CEO of online caregiver platform

"My mom told me to make certain that I truly understand the motivations of people seeking to invest with me. You need to assess the partnership as if your investors were your in-laws. When I pitched VCs, I paid attention to whether partners talked over one another, or if they were on the phone during the pitch, to determine their true interest and their values in respecting entrepreneurs."

Mokhtar Alkhanshali, founder and CEO of Port of Mokha

Port of Mokha imports and sells Yemeni coffee

"My childhood mentor and friend, Nasseam Elkarra, helped me realize that if I pursue my passions, there are only two possible scenarios: You will become an expert in that field and have a thriving business--or you will become an expert in that field and lead a happy life."


Sallie Krawcheck, co-founder and CEO of investment platform Ellevest, author, and former Wall Street executive

"One of my early bosses taught me: Invest steadily, a bit out of every paycheck, in
up markets and down markets. That way you make it a habit."

Katelyn Gleason, founder and CEO of health care tech startup Eligible

"I buckled down to get out of debt after reading this in Benjamin Franklin's autobiography: 'Necessity never made a good bargain.' "

Reporting contributed by Maria Aspan, Lindsay Blakely, Kevin J. Ryan, and Kimberly Weisul.