Ashton Kutcher’s fascinating transition from TV prankster to respected investor

10 min read

03 August 2016

Former deputy editor

Real Business attended the Sage Summit 2016 in Chicago, where one of the guest speakers was Ashton Kutcher. And while the Hollywood star may be best known for his exploits in film and TV, the actor has become a respected investor in over 100 companies, so we've taken a look at the incredible transition.

I’ve thought about it – and entrepreneurs and actors have a great deal in common really.

They often have countless doors closed in their faces before they get their big break, while friends, family and peers can find it difficult to understand the grand dreams they possess.

Although he started off as a model, Kutcher’s looks and charisma secured him a spot on TV and from there he was able to break out into film.

That said, it was TV that arguably generated mass appreciation, and eventually investment potential, for the star ahead of the big screen, as his Punk’d prank show on MTV tricked numerous celebrities with staged scenarios.

Think Jeremy Beadle’s nineties show Beadle’s About, but for A-listers. In his time, Kutcher stitched up the likes of Rihanna, Simon Cowell, Serena Williams, Zac Efron, Miley Cyrus, Beyonce, Justin Timberlake and Hugh Jackman to name just a few.

Opening up on his inspiration for moving into venture capital, however, it was a case of seeing is believing for Kutcher.

“I had a production company that I was running in my twenties and we were building a lot of shows on television. I saw buffering speeds on digital media getting faster and faster, so I started to look at that as a platform for distributing content,” he explained.

“I started looking at various analytics companies to see if we could measure and track the efficiency of the distributed content and started building a digital media studio. The more I looked at those companies, the more I realised how technology was going to have to be in virtually every business.”

Read more from the Sage Summit:

Image: MTV

Seemingly as down to earth as the characters he usually portrays are, Kutcher said the “staggering” efficiencies, creativity and culture of “aggressively successful” startups was the eye-opener that led him on the path to begin making investments in rising tech businesses. Even though it left him feeling daft at times.

“I started investing in various companies and learning by failing – a lot. And learning by sitting in rooms where I was the dumbest person and keeping my mouth shut, listening, and asking as many questions as I could,” he admitted.

Calling the move into the investment space “exhilarating”, he was soon able to find a number of interesting individuals and companies. It was then that he came to appreciate his lessons had put him in a position where he would be able to offer value to startups and the founders behind them.

The actor-cum-businessman went on to launch venture capital firm A-Grade Investments in 2010, aligning with talent manager Guy Oseary and seasoned billionaire investor Ron Burkle. Notable companies the trio has invested in include Spotify, Airbnb, Uber and Shazam, with funding usually in the seed and Series A brackets.

On the next page, read how Kutcher enhanced his enterprise knowledge, why the “aggressive” Steve Jobs approach isn’t his preferred method of doing business, and what he looks for in companies he plans to invest in.

Image: Getty Images for Lenovo

Demonstrating a passion for something out of the spotlight, Kutcher was able to hone his craft with a mentor – an incredibly useful tool that everyone should use to their advantage.

For Kutcher, it was veteran angel investor Ron Conway who took him under his wing, as the Two and a Half Men star said Conway was always open to answering questions. But Kutcher has had many mentors along the way, and encouraged business leaders not to rule anyone out, even if they’re younger.

“I think being willing to be mentored by anyone that you respect; no matter their age or experience, will create ultimate vehicles for success,” he said, wisely showcasing some of that value he mentioned he can bring to founders’ tables.

And that’s a lot of tables Kutcher has to sit at – he has 150 private businesses within his investment portfolio. Interestingly, there’s no set formula that can be replicated to explain his decisions for investing, even with so many firms under his belt.

Sage Summit: Day one – Collaborate and disrupt to become Braveheart of business

Kutcher said of his strategy: “That process changes almost every day. The minute you think you know, you start to see things and patterns that change it.”

That said, the first thing to factor in is the founder and their ideals, personality, ability to overcome challenges and sector expertise. Following that, the product is the next consideration – the understanding, whether it’s disruptive, the competition, the business model.

On the subject of what he looks for as a founder, he used Steve Jobs – a man he played on the big screen – as a prime example. Noting that he is often depicted in films and books as exhibiting aggressive behaviour, Kutcher believes that truly successful individuals are able to “contain emotions”.

“What you find is the people that are generally the most successful have a capacity to contain their emotions, which is the biggest thing, and an open generosity that is so large it almost takes you aback,” he said.

Sage Summit: Day two – Inspiration, innovation and UK-US trade negotiations steal show

“And then they have the humility to ask for help, which is a crazy asset and extraordinary that you don’t think of right off the bat. The humility to ask for help and not know is so powerful because generally these great mentors are willing to give you everything. It’s a powerful quality that I think is missed oftentimes.”

Moving on from the individual, Kutcher offered his thoughts on what makes a great business – it’s one that makes you question your beliefs.

“I think really successful businesses challenge intuition we all have. It’s about being willing to not know. Everybody is so worried about their ego being hurt by not knowing something that they pretend to know things they don’t actually know,” Kutcher said.

As a result, he said that pretence creates false results and failings, connecting non-existent dots.

He proceeded to highlight companies such as Kickstarter and Airbnb as businesses that shouldn’t work on paper, but have in the real world.

Sage Summit: Day three – A new economy has arrived and you're required to give to receive

“Kickstarter is a perfect example. Why in the hell would people be willing to give other people money to build their businesses? With not getting any equity? It’s unfathomable!” he exclaimed.

“Why would people open up their homes and let strangers stay with them? Why?! Any time companies challenge notions and intuitions, those are the companies that play in the grey space where there are no competitors.”

And despite all of the shrewdness and foresight he so clearly possesses, Kutcher demonstrated an affable modesty and downplayed his accomplishments so far. When asked how he wants to be remembered by people in 50 years’ time, he joked to say he wants to hear: “’He’s still alive?!’”

Adding on why that sort of question leaves him cold, and demonstrating the comedy we’ve come to recognise on TV, Kutcher continued: “In 50 years, I’ll be 88, by then my life expectancy should be like 2,000. You know, I hear people talk about their own legacy and I think they’re assholes. Hopefully they’ll say, ‘he’s still building shit’.”

If his current work rate continues alongside the “staggering efficiencies” he’s come to love, building shit in 50 years looks to be very likely.

In addition to Kutcher’s journey, the final day of the Sage Summit also revealed the story of successfully scaling a business is about personal growth.