The Intertwined Nature of the Angel and Entrepreneur Journey

As an advisor for Founder’s Table, WESK asked me to write a post on angel investing for early-stage tech startups. I’m more than happy to oblige, as building their startups will take a village when they first launch. A healthy angel investing circuit will be the first place they should go to through the next phase of growth post-accelerator.

Here’s a slightly abridge version of what I talk about in angel 101 sessions — many of my insights are from lessons learned the hard way. Angel investing is one of the riskiest types of investing, at the earliest stages and often with the least experienced investors. And yet, its one of the best things you can do if you can do it well. It is an opportunity to create an unlimited level of upside for oneself, one’s community and the overall economy with an exponential network effect.

There are certain fundamentals that can be covered through a course like Venture University or books like the Venture Deals by Brad Feld or the Founder’s Guides by Stephen Poland, which were intended for founders but cover the basics well for early-stage angels and investors.

There are a couple programs in Canada that offer angel training and scores more across the US. Experienced, active investors in the US are often open and curious about deals in their northern neighbor, could very well be an opportunity to manage some syndication and support the fundraise for some of your startups.

Your angel profile – what you can offer in terms of additional value add, is what you can bring you proprietary deal flow. This is gold. It means ‘they want you’ and you 100% want that. With every deal, your experience and judgement only gets better. See as many deals as you can. Angel investing requires a trellis mesh of cognitive dissonance. An abundance of logic, intersecting with the most irrational optimism. This is also the ideal mix for growing galvanised founders to climb every stage of the start to scale model, in the hopes of flowering into a true unicorn status. Trellising for proprietary deal flow throughout the ecosystem can be much more effective if you plan ahead.

It takes a certain amount of time and capital to be successful in angel investing. Otherwise, you may as well throw your money on a Vegas craps table. Building out a portfolio is a job in and of itself. Investing in startups is not only about the capital like a publicly traded stock market. You can influence the outcome by offering strategic support – through networks, advise and your own efforts – if you are qualified to do so. If not, give your capital and get out of the founder’s way. Sometimes it can be a situation of infusing capital early and removing it strategically or systematically, so you have pre-set principals enabling you to test and iterate on a process rather than on an emotional level.

Company building is a long-term practice. It’s not predictable, guaranteed or safe. An individual’s risk tolerance, not necessarily their bank account, is a determining factor in whether they participate in this asset class. Expecting a fully baked cake at the beginning of the cooking process is not realistic. Angels can look at the quality of the ingredients to believe in the potential of the founder and their vision. They know it still has to go through to actually, fully cook the meal, that there could be too many chefs in the kitchen, someone can add good or bad advice, the cook could get distracted, miscalculate the timing and burn the cake. But with the right ingredients, the right infusion of knowledge, skill, hard work and team work, the results could be so much more spectacular than the original ingredients or a store-bought cake.

“It is so critical as a female founder of a start up, particularly one who brings an additional and most importantly Indigenous lens of the company, to be true to the purpose and passion of the company and to maintain that focus with potential investors. Investors, “buy into” your story – they can help write the next chapters but it is not their job to take over the storyline – that’s why they are “angels” – watching over, lending support and encouragement, helping us stay true to our purpose and passion, while helping in the incredibly meaningful way of taking a financial risk that our story will resonate for a wide audience.” – Leanne Bellegarde, Akawe Technologies

“For me, it is important to find investors who see the potential of TrailCollectiv to connect families from all walks of life to the outdoors while supporting sustainable and ethical tourism “. – Annika, CEO of Trail Collectiv. “I think it is important to find investors whose goals and experiences align with TrailCollectiv and support our business plan”.