THE THINGS WE'VE DONE, seeN & hearD
Entrepreneurs come in all shapes and sizes. Some build a local business, others take on a franchise, and a few set out to change an industry. Whatever the ambition, the fundamentals remain remarkably similar: build a strong team, manage risk, learn from mistakes, and keep moving forward.
Will Ashcroft’s career has taken him from a small house-cleaning business, which he sold at just 13, to international sport, private aviation, technology, and commercial airline operations, helicopter pilot. Along the way, he has accumulated plenty of achievements—and, by his own admission, more than his share of mistakes. Today, Will is the Founding
In 1995, Ashcroft founded the World Rugby Club Championships, securing a television rights deal that exceeded that of the 1991 Rugby World Cup. In 2006, he launched Jumpjet, helping pioneer the shared private jet market. Over the following decade, he developed businesses across technology, helicopters, and air medical services. His largest undertaking came in 2018, when he and co-founder and friend Rob Caputo secured $450 million in funding to build an aviation group whose operations would encompass 42 Boeing 737s.
His entrepreneurial drive has also served causes beyond business. Following the 1991 Gulf War, Ashcroft took part in more than 20 running events wearing full combat gear including a 50lb pack and boots. These events included marathons, 5Ks, and 10Ks, to raise funds for Operation Support, helping children who had lost a parent in the conflict. With support from Budweiser, the effort raised enough to fund a college education for every eligible child who wished to pursue one. World famous photographer Chuck Rogers gave Will a taste of "15 mins of fame" when he took a picture at the Peachtree Road race in Atlanta. The inaugural Denver marathon was his last and at the end of the race he could be found in the medical tent. But he did it and like many of entrepreneurial activities he never gave up.
Not every idea reached fruition. Ashcroft explored both a submarine cruise venture and a helicopter shuttle concept with Sir Richard Branson; neither materialized. Those experiences are part of a career that has taught him as much about knowing when to step back as when to press ahead.
Featured in more than 200 publications and media outlets, Ashcroft has also appeared in at least three feature films—although viewers may need a sharp eye to spot him. His creative ambitions now extend to fiction and music, with novels scheduled for publication in 2027 and a music album planned for release in October 2026.Will wrote and produced all of the sings on the album but only sings on two of the tracks.
Across these pursuits, the common thread is curiosity, a willingness to take considered risks, and an understanding that success rarely follows a straight line.
1
Why Have a Contact Page If You Aren't Going To Check It
Most businesses large and small have a contact page. But what good is it when you don't check to see who is contacting you. The amount fo small business who ask us what they are doing wrong. The number one item we find is lack of communication with your basic customer.
2
Do You Actually Understand What Business You Are In
Ever heard the saying that Discount Tire is actually in the logistics business not the tire business? Well in order to gain more customers you have to understand exactly what you customer is looking for.
3
Tunnel Vision
Focus. Focus. Focus - The best in the world all have one thing in common they Focus.
4
You Tell Everyone You Have Great Employees
We hear this all too often. "My team is amazing, I have wonderful employees who care, I love my employees........." but do you really understand what they want. A CEO, a good CEO listens let's those amazing employees be great. A good CEO knows how to empower their best people not steal their spotlight.
5
Great Leadership Empowers
Imagine as a CEO leaving early on a Wednesday because your team is that capable! You will never know unless you empower your team and employees to think for themselves without the threat of rebuke for doing so. We all say we do this but it is really hard to do as a founder, CEO or Board member.
6
Jeff Bezos owns less than 12% of Amazon
We hear this all the time. I have to own 95% of my company. Screw the investors they haven't bled like I have..........Well actually they have. They're pretty good at what they do and without them you aren't getting your company funded. Time to take a breath and realize you can be very successful with a little less ego and less equity. You will do just fine.
7
Don't Jump Out Of A Perfectly Good Plane Without A Parachute
Well, don't!
8
Why Are You Calling Me Sir After Our Third Meeting
After three meetings you aren't winning any polite battle by calling me sir. Especially if you want my money. Raising capital is about a relationship. It is not about rank. It is about a relationship and you proving you can be a good manager of someone else's money. So call them Jim if there name is Jim or Bob or Jen.............
9
I hear "NO" a lot. Is our business doomed
Entrepreneurs are like actors. For every big name there are thousands who have never got an audition let a lobe a regular gig on Netflix. Learn from every NO. Remember not every company is going to be the next Google. Your YES might come in a different form. Maybe at about 900-1,000 NO's its time to rethink the model but until then get comfy and use every NO to your advantage.
10
What is an EBITDA
Call us. We can definitely help you. Earnings Before Interest, Taxes, Depreciation, and Amortization. It tell you in truth how well your vision is performing financially and more investors want it to be a positive number. But seriously call us.
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From time to time we will accept a consulting role to help you and your business be better than they are today. We are not just talkers, in many cases we have done it or learned from it. If you think we can help. Please reach out to us. From a start up to a small business.