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From $726K in debt to $3M in 18 months

How admitting you failed can help you scale your business fast.

Entrepreneurship requires a certain amount of magical thinking — the ability to suspend fear, disbelief and doubt so that you can turn an intangible idea into a cash-generating machine.

So what happens when you wake up one morning and realize the magic has run dry? What happens if your business runs out of cash — or worse, plummets into the red? Imagine yourself in those shoes. What would you do? 

If you’re like most people, you’d probably hide the fact from everybody. After all, nobody wants to feel like a failure. And apart from the turmoil of losing everything, no one wants to be seen as incapable.

Could your failure be your ticket to success?

This was the dilemma facing Scott Oldford after the collapse of his Canadian interactive digital marketing agency, Spark Digital, back in 2013.

His bank account reflected a reality from which he’d been hiding — he was $726,000 in debt. And he felt like the magic had run out.

After spending an hour crying in the shower, he decided he would send the news out to the world. But first, he deleted his mother from his email list so that she wouldn’t learn about it this way. He was ready to tell the world, but not quite ready to break the disappointment to his mom.

Although Scott and his business were both seemingly in trouble, that was when the shift happened.

“I decided I was going to let go of the ‘normality’ of what business is and just be me,” Scott explained. Debt was eating at his business like a cancer, but being transparent was his first step to removing the tumor. Had he hidden from the problem instead, it would have only grown worse.

Turning failure into success

Scott decided to flip his story on its head and leverage it to develop a new venture. He realized that before customers buy your product or service, they first need to buy into who you are and what your business is actually about. What people want more than anything is the why behind it all.

For Scott, he learned that he had the ability to get the magic back and turn his business success around. To do this, he would have to tell his story in a genuine way and reconnect with his audience.

By using the formula outlined below, Scott systematically connected with those clients, gained media exposure, climbed out of debt and scaled his revamped business by $3 million in 18 months.

1. Pick a niche

You can’t be all things to all people, so Scott looked for the points where his own experiences and passions coincided with his audience’s pain points. His stories began to resonate because they filled a niche that was specific enough to pique his audience’s interest.

That audience included entrepreneurs who had broken through to the six-figure threshold, but also felt stuck on a hamster wheel — unable to catch their breath. These people often felt more impoverished and stressed at this level than they did when they were making less money.

From this, Scott launched Infinitus, a company that helps six-figure entrepreneurs master lead generation. The company took off and quickly turned it into a multi-million dollar business.

2. Tell the right story, the right way

According to Scott, sharing the raw parts of his story made others feel like they weren’t alone.

This doesn’t just mean sharing achievements or challenges — it means sharing the insights and actions taken in spite of those obstacles. That’s what draws people to you.

For entrepreneurs, it’s critical to always tell your story to the right audience with a tone and voice that will resonate with them. But many businesses end up guessing what makes their clients “pull the trigger” when it comes to a buying decision. Even people who have done the work to define their ideal clients have this problem.

3. Connect with influencers

With social networking and online communities, companies can now create business growth by “borrowing” large audiences from influencers. That’s exactly what Scott did to appeal to the right market. He started to connect with people in genuine ways and develop real relationships.

In addition, actually picking up the phone or meeting clients face-to-face allows you to ask key questions. That method helps you gain a deep understanding of the energy behind your customers’ pain points and aspirations, as well as the exact words they are using to describe those feelings.

4. Find your audience’s underlying motivations

When clients said they wanted more income, Scott discerned that the money invariably symbolized something deeper. These people were looking for more in life — including security, self-worth and love.

By digging deeper and finding the underlying motivations of his clients’ desires, Scott began to relate to different people more effectively. He was communicating in a way they wanted.

5. Look backward to move forward

Struggles can seem easier once you’ve already surpassed them. But those struggles don’t feel easy to someone who’s in the middle of it all.

Realizing this dilemma, Scott forced himself to rewind and relive the emotions of some of the scariest and most painful parts of his life. He shared these personal experiences with his audience, and it began to resonate even more.

By putting words to his feelings, he opened up in brand new ways to his client base. Now, he is able to give his readers and listeners a way to articulate and process their own pain.

6. Always have a clear purpose

Sharing your story is even more valuable when it has a clear purpose, and that can deliver true value in the midst of all the chaos. The only way to achieve that value is to know why you’re sharing something.

Do you want your readers to like, subscribe and share? Are you playing devil’s advocate and trying to stir a debate? Are you looking for people to buy your product?

While these may seem like obvious goals, in practice, many entrepreneurs can lose sight of their objectives. Most entrepreneurs already share posts that are about themselves and their products, but they may not take it beyond the basics of their business offerings.

Scott breaks down his social media posts, blogs and mainstream media appearances into the following categories:

●      Personal philosophy

●      Personal stories and anecdotes

●      Lifestyle

●      Results

●      Questions

●      Invitations

Consider the categories your content can be grouped into, and challenge yourself to find new ways of telling your story. By going beyond the basics, you’ll connect more deeply with your audience, and make memorable connections.

7. Dare to be authentic

By sharing his genuine story and not hiding from his failure, Scott’s business shifted in the right direction.

He was being 100 per cent real, and retained the trust of those who invested in him even when he failed. And by demonstrating that he deeply, viscerally knew his clients’ pain (and had taken the time to process it and share his insight), Scott was able to grow a deeply loyal following.

Now, those people are willing to invest their money into Scott’s business — gaining insights and advice to grow their own revenues.

Telling such stories to ever-larger audiences both on social and mainstream media, Scott has been able to rapidly scale his new company, Infinitus. This time, his company is on track to do upwards of $8 million in 2017, just over two years from launching the company.

Up Next: Do you have what it takes to be the Ultimate Entrepreneur?

What's stopping you from being the Ultimate Entrepreneur?

Geeta Nadkarni

Award-winning journalist, speaker and passionate entrepreneurship advocate Geeta Nadkarni has 20+ years of experience producing print, TV, radio and new media for outlets including the CBC, CNN, Global TV, Reader’s Digest and more and was voted “Best TV Personality” by the readers of the Montreal Mirror. She now blogs for and Huffington Post and is always looking for business success stories to feature in her writing. Her online course, Baby Got Booked teaches entrepreneurs how to do their own PR and has landed students local, national and international coverage within weeks (sometimes even days) of starting. Find out more at and grab some of her free resources or listen to her podcast where she interviews journalists who tell you EXACTLY what they want you to do to get their attention.

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