From turning a US$30 million fund into US$250 million in six years, to making early bets on Uber and Airbnb, he’s built a successful and lucrative investing career.

Kutcher’s money prowess started young

As a kid, Kutcher juggled multiple jobs, including lawn mowing, janitorial work and washing dishes.

Kutcher told Grow, the blog of micro investing app Acorns, which he invested in, that he saved US$1,400 for a snowmobile at age 13. “I worked after school and on weekends for one and a half years, and put every cent into a savings account,” he said.

Raised in Iowa, Kutcher comes from blue-collar roots. His father worked at a meatpacking plant and his mother was a schoolteacher. Kutcher was studying biochemical engineering at the University of Iowa when he was scouted as a model, which ultimately let to his break in the acting world.

Today Kutcher has invested more than US$3 billion into start-ups and taken part in 177 funding rounds over the past decade. This makes Kutcher the most active Hollywood angel in Silicon Valley, according to Business Insider.

“Focusing on this simple goal of identifying and enabling amazing entrepreneurs to create a better tomorrow is the crux of my investment strategy,” Kutcher wrote in a blog post for Atrium, a legal and tech start-up.

What was Trevor Noah’s life like before the models, mansions and millions?

How and why he got started investing

Kutcher said he began investing because he wanted to connect new companies building solutions to everyday problems with the people who needed them.

“I spend a lot of time thinking about new and simpler ways to do things, but don’t have enough time to execute on all those ideas,” he told Grow. “So I found people who were executing on them and invested in their success.”

Kutcher told The Telegraph in 2013 that he was particularly drawn to consumer technologies. “The companies that will ultimately do well are the companies that chase happiness,” he said. “If you find a way to help people find love, or health, or friendship, the dollar will chase that.”

That said, his foray into angel investing kicked off when he founded production company Katalyst in 2000, which led to Silicon Valley connections.

Why millennial millionaires are flocking to California

Kutcher poached Katalyst’s digital chief from TechCrunch, who introduced him to the big names in Silicon Valley. “I spent 90 per cent of my time just listening,” Kutcher told Forbes.

Kutcher soon became familiar with the tech scene. In 2009, at the request of billionaire Marc Andreessen, he invested US$1 million into Skype – 18 months before Microsoft bought the company and quadrupled the value.

A mentor changed his life and how he’d go on to invest

But Kutcher said his investing career hit a new level after reaching out to Silicon Valley angel investor Ron Conway for guidance.

“He is one of the godfathers of angel investing,” he said on his news and entertainment website, A Plus. “He completely opened up his investment portfolio to me and really started explaining how things worked and what his strategy was. He has probably been my biggest mentor.”

From there, Kutcher went on to co-found venture capital firm A-Grade Investments with talent manager Guy Oseary and businessman Ron Burkle. Within six years, he turned a US$30 million fund into US$250 million.

A-Grade focused on early-stage investments, according to TechCrunch. Forbes wrote that these start-ups had to have three defining characteristics: founders A-Grade wanted to work with; a problem-solving mission statement that would make the most of time; and a business model A-Grade could grow.

While there were a few failed investments along the way, such as BlackJet and Fab.com, A-Grade made many successful ones: US$500,000 into Uber, US$2.5 million into Airbnb, US$3 million into Spotify, US$300,000 into Warby Parker, and US$1.5 million into Houzz, among many others. These are all multibillion-dollar companies today.

In 2015, Kutcher and Oseary took a more formal approach to venture investing, co-founding venture fund Sound Ventures with US$100 million from Liberty Media.

Investing other people’s money instead of their own allowed “them to make bigger investments, invest in later-stage start-ups, and put more money into investments that raise follow-on rounds,” according to TechCrunch.

As of 2017, Sound Ventures was managing more than US$100 million in investments, reported The Wall Street Journal. By 2018, it had made over 50 investments and led six rounds of financing.

Its portfolio includes Neighborly, a municipal bond crowdfunding start-up, and OpenGov, a financial tech company for local governments.

These celebrity-owned dogs are living better lives than most people

Kutcher and Oseary told Forbes they’re taking a “typical carry” from Sound Ventures – likely two per cent of cash invested and 20 per cent of profits, plus performance bonuses.

The same year, Kutcher guest-judged on investment show Shark Tank. He was originally hesitant about going on, but felt it “might deliver the opportunity to bring an audience to the show that might not normally watch it,” he told A Plus. “It really is about entrepreneurship and to me the American dream: that you can go off and start something with very little and build something great.”

He ended up splitting a US$200,000 investment with Shark Tank judge Lori Greiner for 15 per cent each of Beebo, a shoulder strap that holds a baby bottle for optimal bottle feeding.

Greiner used her expertise to improve packaging and presentation, while Kutcher used his name recognition, massive social media outreach, and role as a new dad to get Beebo the customers it needed.

Kutcher has three rules when investing, all focused on what he sees in entrepreneurs

The first rule is that entrepreneurs must intimately understand both their product and their industry, he told A-plus. They must also have a personality that will allow them to withstand failure and setbacks, he said.

Kutcher continued: “You can have the best idea in the world and absolute domain expertise and know how to do everything right, but if you want to do something great in the world, there are going to be obstacles; and you have to be a person who has ingenuity and sheer willpower to get through those times.”

The third rule, he added, is that the entrepreneur must get along well with him.

But the real key to piquing his interest has to do with how well an entrepreneur can spin a compelling narrative, he said at TechCrunch’s live Disrupt SF event in 2018.

“One of the critical tests that I try to run when I’m sitting across from a founder is: ‘Can you sell me your idea?’” Kutcher said at the conference.

For Kutcher, the ability to convey a company’s mission determines whether they’ll be able to snag the best talent in a competitive job market. He sees telling the story of an early stage company as integral to its future growth.

“If you can’t sell me, how are you going to sell your first hire, your second hire, your third hire?” Kutcher added. “How are you going to create the capacity for the rest of your team to sell those next hires?”

He’s also doled out a lot of investing advice over the years, often recommending to invest in areas you have knowledge of.

On Chelsea Handler’s Netflix talk show, Chelsea, Kutcher offered up his best investment advice: “Invest in the things that you know. If you drink beer all the time – if you go to microbreweries and you try all kinds of them – you probably know which ones are the best, and my advice is always to invest in what you know.” He also emphasised this in his interview with Grow, where one of his top three tips for deciding on what to invest in was to invest in your own expertise.

Bingeing on Netflix and baking cookies? How Elon Musk spends his free time

And for what you don’t know, he advises finding out everything you can about it. “Know what you don’t know,” he wrote in the Atrium blog.

That involves asking stupid questions. Kutcher advised doing just that at a recent QuickBooks Connect conference. He said that when he was first introduced to key players in the tech world, he would ask every question he could think of.

Learning also requires paying attention. “If you‘re a stock boy in a grocery store and you see something flying off the shelf, find out who made it,” he told Grow. “Find out why it’s flying off the shelf. Do the investigation necessary to know whether it’s something that is going to have ultimate value.”

Kutcher also told Grow you should invest in what you want to see become reality, but approach your vision carefully. “Worst-case scenario, you lose money – but at least you will get the life you want,” he said.

When it comes to implementing that reality, Kutcher has said that while having a vision is important, making a plan is better. At the QuickBooks Connect conference, he advised starting with what you’ve done to work towards your vision or goal, then looking at what you can do next to finally achieve your vision. In other words, nail out the details that get you from point A to B.

Of all his investments, Kutcher said he considers his relationships the best investment he’s made

“Taking the time to get to know [people], what motivates them, what their challenges are,” he told Grow. “These things are often overlooked. Investors get so wrapped up in returns and numbers that they forget that the true privilege of their position is to share a journey with exceptional people.”

His philosophy on investing – and life in general – all goes back to his Midwestern roots. He said he wants to give back to those who need a helping hand.

“I’m very appreciative of the things I have,” Kutcher said at QuickBooks. “I’m always fighting for the little guy, no matter what, because I always feel like I am the little guy. If you’re lucky enough to be doing well, it’s incumbent upon you to help folks who are struggling to grab that first rung on the ladder to start their climb.”

Want more stories like this? Sign up here. Follow STYLE on Facebook, Instagram, YouTube and Twitter .

This article originally appeared on Business Insider.