A change of outlook – Brett Mankey

Brett Mankey is a proud Ashurst alumnus, Board Member, investor and the Executive Chair at Syntrillo, a seed-stage company developing the leading AI-driven software platform for stroke management, prevention and treatment as a chronic disease.

He started his career in London at Ashurst in 1998, working on cross-border M&A, private equity and venture capital matters for companies, entrepreneurs and investors in the communications, media and technology sectors. The legal and sector experience he gained at the firm, together with his exposure to senior decision-makers in many blue-chip companies, including multiple transactions for Deutsche Telekom, has helped shape his career and passion for “building things”. Brett was particularly influenced by partners, such as Chris Ashworth and Tony Ghee, who both gave him many opportunities to get involved in complex deals and interact directly with senior clients. He continues to stay in touch with many of his former colleagues who are now based around the world including Isabella Ferretti in Rome, Joe Connellan in Melbourne, as well as Brian Chadwick, Chris Coulter, Phil Hagan, and Andrew and Charlotte McMillan, all of whom are based in London.

Minimising regrets

Brett’s career has also been shaped by his narrow miss with tragedy. Brett was a ticketed passenger on Flight 77, the hijacked plane that crashed into the Pentagon on 11 September 2001. Three days before his scheduled flight, Brett’s boss, who was the COO of the publicly traded company he worked for at the time, called and asked him to fly out earlier for a meeting. His boss died on that flight. As Brett reflects: “If I hadn’t had that call, I wouldn’t be here. My boss saved my life with that call and it changed my outlook on life. I am determined to live life fully and to always take calculated risks so that I can minimise any regrets.”

Brett spent a couple of very busy years at Ashurst. One of the clients he worked with was AduroNet, where he worked one day a fortnight helping to scale the business. In that role he worked closely with AduroNet’s senior management team, five out of six of whom had previously been CEOs in their own right. That experience, which included AduroNet raising $125 million in one year, became a career highlight, as it showed him how venture-funded businesses grow and scale at a rapid pace. It also gave Brett a long-term mentor who became a close friend – Jeff Donahue. “When I was approached by a few start-up businesses, Jeff, who was an astute businessman and an eternal optimist, gave me some great advice. He said I should ask for a management team seat on the board of directors. I thought that was a crazy notion but the third company that tried to recruit me from Ashurst agreed to that, and three months later I was asked to be the CEO of that company. I was 29 years old running an investor-backed business and soon was raising a $25 million Series B round investment through Deutsche Bank whilst negotiating with the CEOs of public companies trying to buy our software business. As experience goes, it was better than an MBA.”

Brett’s success at an early age wasn’t celebrated by everyone. He recalls driving with the Chairman of the company that ultimately acquired the business he was running at the time to do the final paperwork on the sale of the company and being told by the 60-year-old Chairman that “you are precocious and shouldn’t be doing what you are doing at this age so I am going to teach you a lesson in power.” The Chairman then went on to say he would not sign the papers unless Brett agreed to waive the 12-month severance he was entitled to under his employment agreement. To preserve the jobs of 24 people, Brett agreed to waive it. And he did learn a lesson – just not the one that the Chairman intended. That experience taught Brett how important your personal integrity is and that life’s too short to work with people you don’t like.

Beyond that "lesson", Brett’s been offered some good advice during his career, including to always build and grow your network, always act with integrity, and stay intellectually curious. He’s also received some not-so-good advice, including that it is better to stay in a safe job rather than take an opportunity involving a calculated risk that was on the table.

Driving success

Since leaving Ashurst, Brett’s career has been full of twists and turns, while always being oriented towards technology and deal-making. He has been a CEO (twice), an investment banking managing director, a board member of six investor-funded companies, a general counsel and corporate development senior executive of a NASDAQ-listed tech company and an international transaction lawyer. Along the way, he has gained deep experience in the digital health, internet, SaaS, healthcare, AI, fintech, hospitality, renewable energy and IoT sectors. At this point in his career, he has personally been involved in negotiating almost $20 billion worth of M&A transactions as either a principal or an advisor.

In addition to serving on boards or investing in six other companies, Brett is currently focused on driving the success of Syntrillo, which is in its seed stage, as its Executive Chairman. By integrating wearables, telemedicine, and AI, Syntrillo is determined to effectively manage, prevent, and treat stroke – the leading cause of long-term disability worldwide. Brett and the Syntrillo team, after spinning it out from the University of Virginia, have already attracted significant global investment and interest in the company. They are also confident medical practitioners are now at a point where they are willing to embrace technology to tackle significant health issues like stroke, as the current shortage of medical providers and cost structures make the status quo untenable.

Brett is also part of an informal network of investors who share some of his other commercial interests and who all know each other. Their collective interests include a luxury tequila company, Komos, and a fintech company spun out of Cambridge, EnCloud. The network only invests in companies where someone in the group can directly add value to the business. As an investor and a Board Member, Brett says “I use my Ashurst training regularly to help facilitate, build, and grow things. That training has meant I never feel out of my depth. It’s useful to know more about law than a lot of business people and more about business than a lot of lawyers”.

Outside of work, Brett enjoys fly fishing, traveling, and cooking. He also enjoys gardening when he’s not living in Austin, Texas, where it appears to him that only peppers grow well.

So what’s next for Brett? “I think in terms of five-year plans. I’m not a sailor, but I think my approach is similar to sailing because I keep zigging and zagging to get to the point in the distance where I want to go. I’m currently focused on building Syntrillo, scaling it, and then hopefully selling it for $250m+. By the time I reach my sixties, I would like to be working across or investing in many businesses, rather than focusing on any one in particular. As I’ve also been on a few thousand flights in my career, I’d prefer not to travel as much for work.”