Notes from Last Night: "How to Start & Sell a $15 Million Company"

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What man actually needs is not a tensionless state but rather the striving and struggling for a worthwhile goal,

a freely chosen task.

– Viktor Frankl

As always, another fascinating Esc event last night led by serial entrepreneur Penny Wing and her recent escapee partner in her new venture Brojure – Ollie Codrington. Penny has built and sold 3 successful group travel businesses from scratch and sold each of them in turn, the most recent having sold for $15m.

Key ideas

  • Do something different – be creative, be brave, think outside the box;
  • Failure is inevitable – the secret is to fail fast, fail often and fail as many times as it takes to succeed;
  • There is no harm in having the intention to aim high;
  • Do not underestimate yourself;
  • Micro-test your ideas;
  • You can’t be good at everything – surround yourself with people who are good at what you are not;
  • Do your research;
  • ‘Whether you think you can or think you can’t, you are usually right.’ (Henry Ford)

Penny’s story

Penny started out as an engineer with an educational background in math but through pure chance, sat on a plane next to someone who owned a travel company and who happened to think that Penny’s frequent travel (she had lived in 36 different places before the age of 21) meant she was suited to a job in a travel company.

By the end of the flight she’d been convinced to join his company and never looked back. She spent 8 years in the industry working for someone else, honing her skills and understanding of the industry and then started her first company in 1988, in her living room, with $30,000 in savings. Three businesses later, each more successful than the last, she is on to her next venture with Ollie, who she met on the Start-up MBA course run by Esc.

What struck me as the root of so many of her successes in her many roles was the bold and courageous action based on Penny’s belief in herself and the willingness to do things differently. From the start she approached things differently, refusing to follow her competitors by creating lengthy proposal documents when pitching for business. Instead, she created simple visual one-pagers like brochures, which appealed far more, stood out from the crowd and secured her loyal multinational customers.

She then realised that these brochures could be used by a multitude of different businesses, so decided to set up a software company (Brojure) to sell the program, despite no previous technical background.

You Are More Skilled Than You Think

What I took away was that you don’t always need to have the exact relevant skills to create something successful.

Don’t underestimate yourself. Whatever your background, you will most likely have transferable skills that are highly sought after in any new ventures.

Whether that’s the ability communicate professionally, be organised, manage a team, build great relationships, you are more skilled than you think you are!

To Do an MBA or Not?

An interesting point was raised about the benefits/disadvantages of MBA programs.

Adele shared some of her thoughts having spoken to numerous escapees over the years. The choice to complete an MBA is personal and down to the individual, but question your motivation first. Do you want to do an MBA because you don’t know what else you want to do yet and are using it as another form of procrastination? Do you have that nagging fear that you don’t have the skills to do what you want to do? Is it worth the time and money if you aren’t sure what specifically you are going to get out of it? Are there alternative ways to get the same information but from a less costly source?

I like to think so personally. I feel that I learn in a far more constructive and efficient way by simply speaking to people, reading great books and experimenting in small ways with my ideas. I think that to be truly entrepreneurial you need to do something different, be creative, be brave and since there are so many people doing MBAs then perhaps it is no longer a differentiator. (N.B. Escape the City wrote a book about this question! Available here.)

The Startup MBA

If you really don’t have the required skills for your idea, surround yourself with people who do. Penny’s strengths are in starting a business, growing them big and fast and then selling them. She has no long-term desire to run one company; she prefers to focus of winning big, high value sales contracts. Recognising this, she started looking for a partner to run the business. Cue Esc the city and their brilliant Startup MBA program.

Interestingly both Penny and Ollie may not have been there. Penny was initially discouraged as she seemed on paper to be over-qualified, and Ollie was reluctant to come along as he didn’t have a business idea. Penny convinced Adele that she really wanted to do the course. Adele convinced Ollie that he should come along. As fate would have it, they were on the same intake and have been working together ever since. If ever there was a case study for there being no rules in life and for doing something different, this would be it.

Ollie’s Story

Ollie reflected last night, ‘I can’t remember wanting to be anything but be a lawyer since I was 15… until I was one.’

He was a lawyer as of 4 years ago, but always knew someday he wanted to run his own company. The problem was that didn’t have an idea. His quote above stuck with me as often we have an idea of what we want to and hold on to it so tightly. When we eventually get there, it may not be what it first promised or what you were actually looking for in the first place.

This highlights the value of micro testing your ideas. If you want to be a lawyer, go speak to a lawyer first or shadow one for a week. Figure out what you’d be doing every hour of everyday and the realities of the job before you commit to a degree or training focused on Law.

Similarly with any other venture, if you think you want to be a chef, cook, write recipes, go volunteer in a kitchen, start a food blog. All low risk, low commitment, but will allow you to explore an idea before fully committing to it in an expensive, ‘can’t go back now’ way.

Where Does Success Come From?

A message that came through last night: focus on your strengths and on what excites you.

Ultimately you can’t be good at everything nor can you be passionate about every type of task involved in your business. Penny is excited by going after the big million-dollar contracts and is great at it. So she focuses on that.

There is no harm in aiming high. You have nothing to lose by having the intention to aim big. By leaving yourself open to all possibilities you are more likely to spot opportunities that you may have otherwise shut out.

Another thing to note is that failure is inevitable. Both Penny and Ollie have failed as has pretty much every entrepreneur I have ever heard from. The lesson here is to fail fast, fail often and fail as many times as it takes to succeed.

Also, consider your risk appetite and personal circumstances. Everyone’s different; one person’s shaking hands with a stranger may be another person’s skydive. Just honestly assess yourself.

What They Wish They’d Known

When asked what they would change looking back on their journey so far, both agreed that they needed to have far more software industry knowledge than they first anticipated. They wished they could have ‘seen the road ahead more clearly’. They recommended spending time with people who know what you want to know and learning from them and getting experience in you desired field or industry in any way you can.

Penny remarked that today there is a lot of pressure to grow businesses fast and to make as much money as possible as quick as possible, but maybe there is some value in slowing down and doing a little more research.

The Status Question

As an aside, Ollie brought up a really interesting point around status. As a lawyer he enjoyed being able to walk in to a room and others valuing his opinion and presence. There are a lot of added benefits to do with security, ego, and self-confidence that come from having what is defined as a traditionally successful profession. Even those closest to us find it difficult to accept when you do something less well defined/non-traditional sometimes.

Ollie quoted an ongoing conversation with his mother, where she asks, “But what do you do? What are you going to be?”

“I’ll be your son?’ He suggests. “No? Not enough?”


Sometimes people just won’t get it and that can take a toll on confidence, particularly if it’s someone you care about. Ultimately though, Ollie realised: ‘We all want to be able to look back and have fantastic stories to tell our grandchildren.’ We want to inspire and excite, no matter if we fail or succeed, we’d just like to be able to say that we tried and had a great time in the process.

Talking vs. Action

What becomes clearer to me every time I go along to an Esc event or any else new for that matter is that difference between success and failure boils down to people who do and people who don’t.

If you never stop learning, experimenting, challenging yourself, finding out what excited you and that you’re passionate about, you will always eventually find things that make you happy and fulfil you.

Hey, look, no-one said it would be easy or without some tough decisions, but it’s dawning on me at least, that it really is as simple as getting out there and doing.


Penny and Ollie

Start up MBA:


The Lean Startup – Eric Ries (Start a business in the leanest way possible)

Creativity Inc. – Ed Catmull (Create a truly creative and collaborative working environment, based on the incredible story of Pixar. I want to work for Pixar!)

4 Hour Work Week – Tim Ferriss- (A must read for all escapees. Whether you want to start a new business, become more productive in your current job, do something different, challenge you assumptions about how you work, there is something in here for everyone)


Guest Reviewer: This post was written by Rima Patel. You can follow her on Twitter (@rimapatel7) or on her blog.

Are you based in London? You may be interested in coming to our next evening talk at The Escape School. Details here.

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Frustrated by climbing the corporate ladder, we decided to build a community to help people build meaningful careers doing work that matters – to them and to the world. We help talented people find fulfilling work by making big career changes, building businesses, & going on big adventures. We’d love you to come with us on this journey.

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