About Asher
I'm a serial founder turned CEO coach. Learn more about my work.
My personal mission
Helping founders win
If you are a founder or CEO, you already know it can be the best job in the world and sometimes the loneliest.
I get it. I have been there. I have built ventures from the ground up, led teams from 0 to over 250 people, and raised more than $150 million of funding along the way.
I know the emotional highs and lows that come with scaling a business and the weight of having the final call when the stakes are highest.
After years as a founder, operator, investor, and now coach, I have learned that great leadership is not about having all the answers. It is about asking the right questions and creating the space for clarity and decisive action.
Today, I coach founders and CEOs full-time, partnering not only with ambitious individuals but also with leading VC funds including Octopus Ventures and Cherry Ventures to support the growth of some of Europe's most promising technology companies.
My journey at a glance
Founded first company at age 17
Achieved two successful exits
Built and scaled teams from 0 to 250+ people
Raised over $150 million in growth capital
Made 45+ angel investments in early-stage ventures
Led companies across Toronto, Silicon Valley, New York, and London
Coached over 100+ founders, CEOs and Investors
Coaching Partner at Octopus Ventures and Cherry Ventures
My background
Hi, I’m Asher. Serial founder. Investor. Trusted CEO Coach.
My journey has always centred around supporting ambitious ventures and the leaders who drive them. Long before coaching CEOs and founders, I was building and scaling businesses myself across Toronto, Silicon Valley, New York, and London — an experience that's given me a uniquely global perspective on leadership, strategy, and growth.
My entrepreneurial story began early when I founded Make it Matter, one of the world's first crowdfunding platforms, enabling thousands of creators to bring social impact projects to life. After successfully exiting that business, I joined Boston Consulting Group, advising senior executives at major global corporations on strategy and organisational transformation.
Driven by a desire for more hands-on impact, I worked for the CEO of Skype, leading strategic initiatives during a pivotal time for the company. Initially preparing for an IPO, Skype ultimately accepted an $8.5 billion acquisition offer from Microsoft — an outcome I contributed to directly, including helping craft the deal presentation that was shown to Bill Gates.
Entrepreneurship called again, leading me to found Midrive, the UK's leading digital-first driving education and insurance platform for young drivers. Midrive scaled rapidly to over 200,000 users before being acquired by The AA in 2020. Most recently, I founded Uncapped, the UK’s fastest growing fintech in 2021. Since launch, it’s provided over $500m of funding to other startups across the UK, US, and Europe, raising from top investors including Seedcamp, Lakestar and Moro Capital (Santander).
In 2017, I was honoured to be named Emerging Entrepreneur of the Year, and in 2020 entered into the Entrepreneurs Hall of Fame.
However, my path has also included tough lessons: shutting down a business, navigating burnout, neglecting friendships and my partner, and learning to cope with the intense pressure that leadership can impose on personal wellbeing. These experiences deeply shaped my approach to coaching, grounding it firmly in empathy, practicality, and real-world understanding.
Today, I coach CEOs and founders directly, as well as serving as a Coaching Partner at leading venture capital firms, Octopus Ventures and Cherry Ventures, trusted to help their portfolio CEOs unlock growth and accelerate performance. My clients lead some of Europe's fastest-growing technology companies across fintech, health-tech, and consumer brands.
My greatest joy comes from seeing founders I coach achieve breakthrough success, not just professionally, but personally too.
If you’re a founder or CEO ready to level up your leadership, I’m here to support you on your journey. Get in touch.
My coaching style
Clients describe my approach as practical, direct, and deeply empathetic.
I create a space where you can be honest about your biggest challenges without judgment. We focus on the real-world decisions you are facing today and the leader you are becoming tomorrow.
Every session is designed to help you move forward with greater clarity, sharper focus, and more confidence.
Why I became a CEO coach
When I was a CEO, I struggled to find a coach I could trust. I wanted someone who not only understood the role but had actually been in my seat before.
After exiting my last venture, I didn’t want to just sit on the beach. And what I loved most about company building was helping people grow. Now, as a coach, I get to do exactly that. I get to be the partner I wish I had when I was navigating my toughest leadership moments.
Coaching is not a side project for me, it is my calling.
How I'm different
I am not just a CEO coach. I am a trusted advisor.
I combine coaching with strategic advisory, acting as the board member you wish you had: someone whose only agenda is your growth and success.
Where many coaches avoid offering opinions, I believe the best founder coaches offer both space and guidance, drawing not just on coaching frameworks, but also on real-world experience leading, building, and scaling companies. You can read more here about what is involved in CEO Coaching.
With me, you get a partner who can meet you where you are and help you get where you want to go.
Want to learn more?
A unique CEO coaching program tested with 100+ founders
I use a three part approach to help founders level up themselves, their teams, and company
1. Awareness
I help uncover strengths, blockers, and blind spots through assessments and a 360 review. We then build a clear CEO Development Plan tailored to your next stage of leadership.
2. Action
In one-on-one sessions, we focus on your most pressing challenges across Self, Team, and Company. You leave each conversation with sharp next steps that drive momentum.
3. Acceleration
Between sessions, you access ad-hoc WhatsApp support for real-time challenges. You also can supplement your growth with curated exercises and readings to embed learning.
BUILDING SOMETHING GREAT?