How to Survive Your First Venture: Lessons We’ve Learned Through the Years

In 15+ years of investing in startups, I’ve learned a thing or two about growing a company. There’s no question about it, my partners and I have seen the most success funding repeat entrepreneurs. Serial CEOs not only have the confidence needed to lead the strongest teams, they also have some invaluable lessons learned in their back pocket. Often learned the hard way, these lessons save companies time and money.

Her are some tidbits of advice, learned from funding my own company and picking the brains of some of the savviest entrepreneurs in Canada.

Go big or go home

Targeting your biggest customer first is hard because it means going completely out of your comfort zone right away. Marcel Lebrun, CEO of legendary tech company Radian6, used this tactic and it paid off — big time.

Trust your gut

Like most things in life, if something — a partnership, a deal, a strategy — does not feel right, it probably isn’t. This advice comes from serial entrepreneur and CEO of nGUVU, Pierre Donaldson. Many first time entrepreneurs fall into the trap of “trying things out for a little longer”, which often ends up wasting time.

Hire smart

A great culture doesn’t just happen, you need to build it. Never hire someone if you have a doubt, it’s much wiser to grow the team meticulously than rush and hire the wrong person.

Choose your VCs wisely

When you are talking to VCs, make sure your visions are aligned right from the initial meeting. Good partners will be an integral part of your company and you need to treat them as part of your team.

Beg, borrow, steal

It’s ok to take some shortcuts and imitate aspects of other successful companies. You don’t need to reinvent the wheel — the savviest CEOs use commonly used best practices and find ways to bypass a more complicated route. A great example is how Airbnb used Craigslist to kick start its listings!

Stay hungry and don’t give up

One of our most successful portfolio companies’ CEO admitted to me that more than one, he was at our door, about to walk in and ask to give our money back and move on because it was too damn hard. He didn’t end up giving up, and his relentlessness made him the successful CEO he is today. It’s completely normal to go from feeling on top of the world one day, to wanting to abandon everything the next. That’s just the nature of startups!

Treasure your customers

Your customers are your most valuable assets, and the best CEOs treat them like kings & queens.

I hope you enjoyed our first (of many!) blog post. We’re excited to share more insights on Venture Capital, entrepreneurship and Canadian startups.