In this edition of Lived It, we sit down with Heather Payne, Founder and CEO of HackerYou— Toronto’s best full- and part-time courses for people who want to learn to code. Heather has been angel investing since the age of 24, and is passionate about supporting other young entrepreneurs.

When we ask Heather to name other female angel investors that she admires, she pauses, it takes quite some time for her to come up with a name. While Heather humbly suggests the fact that names don’t immediately jump to mind is due to the fact that she’s not very active in the angel community, we’d challenge that to say it’s simply a symptom of the fact that – until now – there really hasn’t been a place for women angels to go to get connected with other women like them.

In this interview, we talk to Heather about everything from the lack of female role models in angel investment, to how she got started as an angel investor, how she approaches deal-flow and negotiations, and we collect tips for other women looking to make their first angel investment.

First Investments

Heather’s first investment was in Katherine Hague, and her first company – ShopLocket. If ShopLocket sounds familiar, that’s because it was Heather’s willingness to take a leap of faith and be the first to invest in Katherine’s company. Two years later the company was acquired by PCH — that ultimately inspired Katherine to start angel investing herself and to launch Female Funders, in an effort to encourage more women to follow in Heather’s footsteps.

Heather would not describe her investment in ShopLocket as being particularly rational at the time. Heather had just quit her job to work on Ladies Learning Code [the non-profit precursor to HackerYou] full-time, and Katherine who quit her job on the same day as Heather had started working on ShopLocket.

Heather was living off of her savings. “I think I probably had 20 grand in the bank. My rent was 1350 a month. So it wasn’t a great situation,” Heather said when reflecting on her financial state at the time. Heather and Katherine had only know each other a few months, but had started getting together regularly to chat about startups, and their mutual aspirations and challenges as new founders.

“I think I probably had 20 grand in the bank. My rent was 1350 a month. So it wasn’t a great situation.”