Overnight Success is Decades in the Making

December 6, 2023

A year ago, I officially started fundraising for Staircase Ventures Fund I.  Fifteen weeks later, we completed our first close of $22 million for a $25 million target-sized fund.  Five months after that, we completed our final close, at an oversubscribed $34 million.  It typically takes a new fund 12 to 18 months to get to a first close and 24 months to get to a final close.  Why was  Staircase Ventures able to do this in less than half the time, in one of the most challenging fundraising environments in decades? 

The answer is consistent across virtually every “overnight success”: it was many, many years in the making.  Significant success is always preceded by relentless determination, discipline, dedication, and resilience over a very long time.

I am frequently asked, “How did you close an oversubscribed fund in less than nine months, in an extremely tough market?”.  My answer is: “I did not close a fund in less than nine months.  It took me 30 years”. 

When Jon Rahm won the Masters earlier this year, he earned $3.24 million over four days.  Or did he?  He only won because he had been playing golf for 25 years, working hard every day, making sacrifices, displaying discipline and determination, continually learning, overcoming setbacks, and never giving up.  He won $3.25 million in one weekend, because he had worked hard for 25 years.

This is a common theme as I think about the founders and companies that I have worked with over the years: people often work diligently, relentlessly, with passion and purpose, for years before they see tremendous success.  Caitlin MacGregor founded Plum.io eleven years ago but only in the past two to three years has the company seen breakout growth, industry awards, and global recognition.  She quadrupled revenue over the past 3 years because she spent the preceding 8 years learning, evolving, and laying the foundation.   

Shopify’s roots trace back to 2004 and it took more than six years before the company raised a relatively modest $7 million Series A.  Four years later, Shopify was valued at over $1 billion, and the company went public the following year.  Yet it was those early days of Tobi and Scott running an online store for snowboarding equipment that gave them the motivation and insight to create Shopify.

Thirty years ago, when I began my career, I committed myself to abiding by the highest ethical standards, treating others with respect and care, making a significant and positive impact, consistently exceeding expectations, and maintaining a strong work ethic.  These commitments have been the hallmarks of my professional journey and formed the foundation that enabled me to build a successful track record, both as an operator and investor, while building strong, trusted, and respect-based relationships.  Raising Staircase Ventures Fund I ahead of schedule, above target, and in an extremely challenging environment was only possible because of what I had done in the preceding 30 years.

Most investors in Staircase Ventures have known me for many years, and all made their decision based on my 30-year track record, reputation, and our trust-based relationship.  The first $1 million commitment came from someone who worked with me 20 years ago.  Three others came from people who have known me for 30 years, and two more from people who have known me for 25 years.  They have watched how I work, the values I hold, and the determination and passion I bring to every endeavour. 

My advice to anyone looking to build a long term, successful career is to:

  • Play the long game in everything you do.

Do the necessary work today so you can get to where you want to be in the future.  Think long term and every day, lay the foundation for your 20- to 30-year goals.  This involves planning and taking initiative.  It also involves dedication, as there is no substitute for hard work, disciple, and hustle.  Ambitious, determined entrepreneurs who aim to build an enduring company understand this and act accordingly.

  • Generously and abundantly help others with no expectation of return.

Staircase Ventures’ first value is to embody a “give-first” mentality.  We help others without the expectation of getting anything in return.  I have found that the most successful people embrace this philosophy; they consistently go out of their way to help others, not to advance their own cause, but because they have a generous, giving approach to life.  They live with an abundant mindset rather than a scarcity mindset, and this ultimately attracts people, opportunities, and resources back to them.

  • Get determined, not discouraged.

When I decided that a classifieds platform could be successful in Canada, I was told by many people that there was no way Kijiji could win in a market where Craigslist was already the dominant player.  When I decided to launch my own fund in late 2022, I was told by a colleague that there was “No f— way you are gonna have a first close in Q1”.  I love to prove people wrong.  Anyone who is starting and building a business is facing tremendous odds and will have people tell them that they will not be successful.  How you respond to setbacks and doubters has a huge impact on your future.

What will you accomplish in 20 or 30 years?  Whatever it is, it will be determined by the actions you take today.

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