One idea to Build your Business, one idea to Scale your life. Every Wednesday.

Welcome to Winformation Weekly. My 13 years’ experience of growing a business from £0-£100m, and the life that goes with it. All wrapped up, in one winning weekly email.

Simon Says

Winformation This Week…

I once caught an episode of How I Built This with Guy Raz, featuring the incredible Sarah Blakely. Her story is nothing short of unreal. She turned a $5,000 investment into a $1.1 billion business and has managed to retain 100% ownership of Spanx to this day. Honestly, she doesn’t get nearly enough recognition. I’ve been hooked on her journey ever since. In today’s Business Section, Sarah reveal’s her approach to risk, and how her father shaped this from dinner table chats as a kid. Today’s Life Section is all about habit, and how to think about the notion of bouncing back quickly once momentum has been broken.

Business

Lessons From the Dinner Table: What Billionaire Founder Sarah Blakely Teaches Us About Risk

Back in the late 1990s, Sara Blakely was selling fax machines when she had the idea for a product to “shape” the female body using undergarment clothing. She invested a few thousand of her savings to patent the product. Today, she is the billionaire founder of Spanx. When she started, she knew nothing about the product she was trying to launch. Why would some people see this as a huge risk and keep it firmly on the “dream shelf” and yet Sarah go full throttle at the idea? Here are Sarah’s tips when it comes to risk taking.

Embrace life. Unlike so many, Blakely is not afraid to try things, even if she was deemed by society as a failure. She credits her dad for not allowing her to have fear. “He’d encourage us to fail,” she said. “He’d asked us what we’d failed at that day, which at the time was confusing, but looking back I understand he was redefining failure. So, failure wasn’t about the outcome, it became about not trying.”

Bootstrap yourself. Despite having no experience in the fashion industry or any investment, Blakely put her savings into her idea. She didn’t quit her day job right away, but she didn’t dilly dally either. She used her savings to start the business and when she became a billionaire, she still owned 100% of the company.

Innovative thinking. Blakely took a risk by challenging the conventional hosiery market, focusing on creating a product that was radically different. Her success highlights the value of trusting your instincts. “I think of a lot of ideas at traffic lights,” she says. “I pay attention to things that haven’t evolved and why. I ask myself questions all day, every day. I could be looking at a table and be like, ‘why is the table like that? When was the table first created? Is that the actual best design for a table? Or could there be something different?”

Personal resilience. She faced numerous rejections early on but remained determined. “As an entrepreneur, working against self-doubt is constant. The only way to find out is to completely put yourself out there and see if you sink or swim. It’s a risk on the biggest stage. If you're doing something disruptive... it's going to look weird, unfamiliar, crazy etc. But shouldn't that be the goal?” That is not to say Blakely didn’t have focus, as she explains: “I didn’t have any employees, no patents, and no clue what I was doing. But I had a really clear vision, and I was willing to do whatever it took to make it happen.”

Life

The Habit Jacuzzi Effect: How to Bounce Back When a Habit Streak is Broken

They call Monday, 20th January, "Blue Monday," whoever they are. It’s supposedly the “saddest” day of the year, and the reasons given are pretty relatable. Most people haven’t been paid since the financial blowout we call Christmas, there’s no holiday booked to look forward to, and we can’t overlook the fact it’s a cold Monday too! But the main reason? Apparently, 88% of people have already given up on their New Year’s resolutions.

Whether you set resolutions or something similar, "quitting" often just means a new habit has been broken, not permanently abandoned. It really gets to me when people say they’ve “quit.” Every habit streak gets broken at some point. The real magic lies in how you respond. James Clear’s advice from Atomic Habits "never miss twice" is a gem. Skip a workout? Make sure you’re back at it the next day. Have a cigarette after a 10-day break? Make sure the next 11 days are smoke-free. Streaks will break, but progress comes from how quickly you bounce back.

When I coach people on getting back to their goals and habits, I use an analogy that seems to resonate: Imagine the last time you went swimming. You’re in the main pool, and the water feels just right not too warm, not too cold. That’s you on a habit streak, ticking off tasks, on top of life, and making solid progress. You’re feeling proud and productive. Then you think, “I’ll just sit in the jacuzzi for a bit.” You hop in, and it’s warm and soothing. The bubbles are relaxing, and you’re not moving at all. You deserve this little break. But after five minutes, you decide to get back in the pool. Suddenly, it feels freezing and uncomfortable. You wonder, "Do I really want to swim again, or should I just get out and go home?" The jacuzzi represents life’s interruptions, a holiday, moving house, a three-day illness, or a big work project. It halts your momentum. When you try to get back into the pool (your goals and habits), it feels uncomfortable. Has the water gotten colder? No, it’s the same as when you were feeling great just a few minutes ago. Starting and resuming share that initial discomfort. But the key difference with resuming is knowing that you’ll adjust again.

So next time you feel like quitting, remember: the water hasn’t changed. You just need to jump back in.

Until next week! 

Let’s win, together!