Four founders share what they’ve learned

People say that hindsight is 20/20. After working knee-deep in the trenches for a year or two, you gain a better appreciation of where to focus, what to let go, and how you can do things (or should have done things) better.

There’s no shortage of advice out there for startup founders. But since entrepreneurs are usually the best qualified to give fellow entrepreneurs advice on how to deal with the challenges of the job, I’ve asked several portfolio founders to share the invaluable lessons learned from their own journeys. What follows below is a snapshot of insight and advice from these great individuals. I’ve divided their thoughts by topic: company focus, scaling the organization, firing, metrics, diving deep as a CEO, and listening to advice.

Enjoy, and feel free to continue the conversation in the comments area…


On product/company focus:

“One of the things I’ve learned is that as an early stage start-up, you have to do only one thing well and one thing that connects with the users. There is no need to build something that will overtake the world right away. The vision has to be there, but to get started you only need to get one thing right.”

– Ethan Song, Frank & Oak


“Don’t obsess over competitors. In the early days we used to panic when someone popped up with a similar offering. However, we can’t be everything to everyone and others will come in to pick up the pieces of the market that you are not addressing (or not addressing well). Rather than worry about this, obsess over your customers and stay focused on addressing your most profitable growing customer segments.”

– Rick Perreault, Unbounce


On scaling the organization:

“As we scale, I’ve realized how important it is to go from a founders led company towards a management led company by bringing the right guys on board. That’s where hiring guys that are smarter and more experienced than I am has made a huge difference.”

– Ethan Song, Frank & Oak


“You probably need to hire your Director / VP-level executive team members much earlier than you think. As the CEO, you are the least scalable part of your company, and if you’re in rapid-growth mode you’ll find your time will rapidly evaporate as your growing team seeks your input and advice on key decisions.

So, hire excellent lieutenants that you can trust as early as possible, and trust them to execute. Hire the best people you can afford in these roles, as you need to trust them to run with and execute on their mandate. Focus on high-level goals and vision, and trust your team to execute.”

–        Jack Newton, Clio


“Building a team and keeping the entire team motivated and aligned towards the vision is also much harder than it seemed. I wished that I had put more focus on this earlier on.”

– Ethan Song, Frank & Oak


On metrics

“I wish I had understood the importance of reliable business metrics earlier on (and I don’t mean Google analytics). We were in business nearly 18 months before we realized that we were losing money on one customer price plan.”

– Rick Perreault, Unbounce


On firing

“You may find that you’ve made a bad hire, and you’ll know it in your gut just a few weeks or months into their time with your company. First time CEOs (and managers in general) are much too reticent to part ways with bad hires, and err on the side of giving the new recruit too many chances to improve or change. I’ve found you rarely, if ever, see the turnaround you’re looking for – you’re much further ahead making a quick decision if it’s not working out, and part ways.”

– Jack Newton, Clio


On diving deep

“You don’t get to deep dive on things as a CEO, but you have to do everything to the right amount of depth.”

– Kyle Vucko, Indochino


“The most difficult balance to strike as CEO is deciding what level you need to be involved in various decisions – not micromanaging (because you can’t scale), but not completely abstracting yourself from key aspects of your business, or putting blind trust in your executives. As CEO, you need to deeply understand every area of your business: sales, accounting/finance, support, product, marketing, etc. You simply can’t afford to have any ‘black boxes’ in your org chart.”

– Jack Newton, Clio


On listening to advice

“You will be most successful if you lead from a place of self.  Everyone has opinions on what you need to do, where to focus, what to hire for, how to approach tough decisions, how much/little info to share, etc. Their opinions are generally true, but you have to put your unique spin on it. The ‘what’ can be learned from others; the ‘how’ is unique to you and must be honed and honoured.”

– Kyle Vucko, Indochino


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