#TechVAN: Annalea Krebs on getting past bad startup days

#TechVan Annalea Krebs

As an entrepreneur, what was your worst day in a tech startup and how did you get past it? When do you pivot, and how do you pull it off? These were some of the questions discussed by entrepreneurial presenters at Vancouver’s ever-more popular tech community gathering, TechVancouver. Hosted at the Rise in downtown Vancouver on Tuesday, the meetup played host to tech CEOs, coders, dreamers, and learners, as well as tech company recruiters who were looking to hire this week. Social Nature CEO Annalea Krebs kicked off the evening’s presentations with a talk on how to get past those big bumps in the road. (Related: See BetaKit’s coverage of presenter and Tagga founder Amielle Lake’s ideas about how startups can find their value proposition).

Bad days and business mismatches

Krebs has sometimes been called the queen of green for her previous role as the founder of Ethical Deal, a bootstrapped startup that she sold before moving on to her latest venture. From her vivaciously positive personality, you might get the impression she’s never had a bad day in her life – but the reality of a scrappy entrepreneur is very different.

“Even when you’re up at the top, you’ve got to remember a low is coming. But the opposite is also true, so calm down when something great is happening.”

“Being an entrepreneur isn’t glamorous most of the time,” Krebs noted. “But I get my inspiration from the pain.” She recalled her first moment in business, immediately after graduating from Royal Roads, and depositing $25,000 into an account for Ethical Deal. Full of big ideas and enthusiasm, she started looking for a technical person who could be her CTO and take her vision of a green Groupon-style marketplace into reality.

“I hired him because I got such a passionate response, telling me that if he didn’t apply for this he was going to regret it for the rest of his life,” she said. Just one detail: the technical person was answering her ad on Craisglist. First mistake. Second mistake? Not realizing in the brief hiring interview that their goals weren’t in alignment.

One of Krebs’ worst days came just as her online platform went live – and her CTO quit. “There was still lots of development to be done, but no more money in the bank.”

Just when the company should have been celebrating and starting to compound their successes, they were stuck. “I wanted to build a business,” she explained, “but he just wanted to build a product and that was the end of his entrepreneurial journey.” After getting past that and negotiating even worse days ahead, she met with success in the sale of her startup – but the lessons of the hard days still stay with her.

On growing, pivoting, and painful choices along the way

As Ethical Deal grew, the good days got better, but the bad days – well, they were bad. She recalls the time she was changing up the business fundamentally – and that meant chopping jobs. Up to half of her workforce was going to have to go.

“Having people quit or firing people is the worst day, any day,” Krebs said. “Those days can never get better. What was painful was that as I was looking at the next iteration of our business, I was considering who I could carry with me to the next business model.” Not everyone would make it.

In trying to mitigate the fallout, she ended up hurting the company. “Some, I tried to find a new home for,” Krebs explained. “I tried to straddle both business models and find a place for everyone. The result was that the workspace became toxic. Employees didn’t know if they were in the new business model or the old one.” The lesson: don’t drag the process out. If you’re going to change, then change.

Wrapping up, Krebs noted that those ups and downs, good days and bad days, are just pinpoints in an entrepreneurial journey (that hopefully is moving upward and onward over the longer term). “There will be highs and lows. But even when you’re up at the top, you’ve got to remember a low is coming. It’s never as bad as it seems. But the opposite is also true, so calm down when something great is happening. It’s a journey.”

Jonathon Narvey

Jonathon Narvey

Jonathon Narvey is a content marketing strategist and BetaKit Senior Editor. Living and working in the heart of downtown Vancouver, he's watched this city's tech hub grow and start to compete on a world-class level. He has learned most of what he knows about tech startups and entrepreneurial spirit by interviewing some of the most innovative thought leaders here and abroad. He's always up for learning something new about the startups, leaders and technologies that are changing our world.