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The unreasonable complexity of private investment paperwork

In general, driven by regulations and risks, standard legal contracts grow and grow in complexity until they become unworkable. In the world of private investments, we’re at, if not past, that point. In the U.S. (and most of the developing world), private investments into startups and funds is regulated, allowed only by rich and/or experienced investors. “Private” in contrast to the public...

Everyone has a mission

Sitting here at Impact Hub Seattle, a member of Toniic and Investors Circle, and a teacher at Pinchot, I’m surrounded by thousands of entrepreneurs, investors, philanthropist, and employees who all work for mission-driven organizations, both nonprofit and for-profit. The one commonality across all of that is that everyone has a mission. Back in my days in tech, this wasn’t true, at...

Aviary.vc takes flight, expanding Fledge, and re-branding Kick

My 2016 is shaping up to be quite exciting: Aviary.vc – To keep up with the growth of impact-oriented entrepreneurs, Aviary is a new venture capital seed fund, focused on mission-driven for-profit conscious companies, i.e. companies that do good by doing business.  If you are an accredited impact investor (or wondering how to do that), we’re building a community of co-investors.  Contact us for...

Valuation, a big difference between Angels and VCs

Outside of California, where it feels like all investors are professional investors, and following up on last week’s post about one difference between Angel and professional investors, another difference is the way the deal terms get set, especially valuation. First-time entrepreneurs don’t understand how startups gets valued.  Neither do first-time startup investors. In my MBA class...

Dealflow, the difference between Angel and professional investing

As an entrepreneur, I’m well experienced at wearing multiple hats and in such, in viewing companies through a multitude of lenses: production, marketing, sales, finance, etc. The same is true as an investor, where I swap between two distinct hats: Personal and Professional investor. You’d think these two hats were identical, but they are not.  They are complimentary, but are two quite...

Native or Imported Entrepreneurs?

An ongoing discussion during the Investors Circle trip to Nairobi was about the tradeoffs between the companies founded by Africans and those founded by Americans, Europeans, and Indians. We met a few of both, and thus had a first-hand look to make (anecdotal) comparisons. Overall, the consensus was that natives like GreenChar and Totohealth had the advantage of deeply understanding their market...

The 140-character (Tweet) pitch

Entrepreneurs fret over the 30-second “elevator pitch”. In my twenty years starting startups, I did twice pitch in an actual elevator. But here in 2016, entrepreneurs should be fretting more over their 140 character, one-line “tweet pitch”. Why is this so important? Simple. Your startup is going to listed on a dozen sites online, and all of them will include that one-line pitch: LinkedIn, Angel...

Novel, but Certain (to Work)

The more one dives into startup investing, the most one finds Catch-22’s.  This post is about the tradeoff between being inventive and copying a known business model. Novelty.  The risk-averse investors who make the high-risk investments in startups tend to like new ideas.  They are early adopters of new ideas and new technology.  They enjoy the excitement that comes with novelty and...

Assuming everyone wants an exit

The last time I presented at an event for investors, the first five people all asked me the same question, “Any exits yet?” The more years I spend focusing on revenue-based investing, the more that question is getting on my nerves.  Perhaps some of that is on me, as the talks I give are generally titled “Investing without Exits” or “Alternative Exits” or...

The problem is that you don’t tell us how you make money!

My morning today includes 18 pitches at the quarterfinals of  Social Venture Partners Seattle’s Fast Pitch competition.  18 first-time entrepreneurs, each with just five minutes and no Q&A, hoping to impress the judges enough to make it to the semi-finals. It’s a tough format. 40 judges in auditorium seating in a University of Washington classroom.  40 judges staring down on the...

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