10 Nov 3 startup pitch lessons (disguised as 3 lessons for a new startup investor)

Published on Medium at https://medium.com/@nbloom/3-startup-pitch-lessons-disguised-as-3-lessons-for-a-new-startup-investor-79778838cdb2

One month of wading into the exciting world of startup investing, and I have been pummelled with lessons of the pitch and the grokking that an early stage investor must do. I can’t stop but accumulate a list of lessons learned. What are lessons for investors, in fact, are lessons on how to make a pitch great.

Early stage startups are risky. Investing in them leads to growth or, more likely, zero. The signals are incomplete. The value proposition is likely still not verified. Early stage investors still aim to codify their due diligence, and there is no universal or right or best way to do this.

The challenge is to measure internally the risk of the company. Once the investor finds a company behind a threshold of interestingness, either he gauges it as too risky or comfortable, or, so often, unable to be discerned. What’s most intriguing, I’ve found, is how to get from “unable to discern” into a investment decision — yes or no.

1) Pitch transparency of risk. I’ve been guilty when pitching investors, from the other side of the table, as an entrepreneur, to make the opportunity seem big and certain. She can speak on the strengths, and dance around the weaknesses (ideally as nondefensively as possible) when probed. But the investor is inherently skeptical. Of course there are massive risks. What are the biggest ones? What is the outcome if they come to fruition; have you proven there are alternatives to your playbook? Or how are you even thinking about this? If an entrepreneur can build a transparency around the risks, preemptively, and explain what they don’t know and how they are constantly thinking about it, it in fact comes off as more confident and lets the investor measure more accurately that risk factor in their head.

2) Memorable something. I’ve joined some larger pitch events, which are not interactive on the fly. Sometimes, you leave with one memorable bit that you can’t help but want to tell someone or your partner later that day: a problem that seems so viscerally important and here’s this neat little solution, impressive traction (from launch to $1M ARR in less than a year), daily engagement of the app, even high NPS. It is up to you to decide what you want that to be (or rather instead of other the investor guessing, fumbling, and forgetting). And you want to repeat it at least 2–3 times.

3) Blend of the past and the future. The great, confident founders can legitimately say that the current product makes them feel embarrassed. They already have a beloved product used by millions or paid for by the thousands. Another founder may emphasize what they’ve done to date: substantial growth that will continue. Still, that’s not enough. A less confident founder may talk endlessly about the things coming down the pipe — a hire, funding close, upcoming product launch, or feature release that will be the supposed panacea. Yes, that’s lacking too. But when the founder strikes a balance between what has brought you to this point, and also what drives you to soldier forward, it is tremendously powerful. On one side, what is your success to date; on the other, why are you doing this, and how can this continue to drive the team forward. Even if that vision is so stupendous or lofty, it’s a signal of passion.

I have about 15–20 more lessons to continue this post another day. Stay tuned!

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01 Mar Does AI want to be humane?

Published on Medium at https://medium.com/@nbloom/does-ai-want-to-be-humane-1ea354e6832e#.gqhttg99i

I had this little exchange recently around a Vancouver tech conference. Here are a few reasons that there’s a common fear about AI: sci-fi movies, the Turing Test, and Kurzweil.

Is it ever easy to overanalyze these sci-fi movies about their critique of our culture or our future:

Why does Alex Garland’s 2015 sci-fi flick Ex Machina show that the pinnacle of AI is convincing human-like emotion? Or that the flaw of the human is their susceptibility to their emotions or to their empathy? And, did that Ava character pass the Turing Test? Well, in a condensed, feature-length film tackling big issues and trying to entertain, ambiguity is your friend.

Feelings! Ava from Ex Machina

Feelings! Ava from Ex Machina

“The Turing test is a test, developed by Alan Turing in 1950, of a machine’s ability to exhibit intelligent behavior equivalent to, or indistinguishable from, that of a human.” The Turing Test is often seen as the definitive threshold for AI to be “true intelligence” and gets frequently name-dropped throughout pop culture.

Programs are already beating and tricking humans at chess and games, music composition, and even poetry. Disappointingly, often, AI programs will pose as a foreign-speaking child to slacken the judge’s scoring. Sure, it’s likely this confused and unintelligible “person” just doesn’t know very much!

I’d prefer to hear from voices in AI like Stuart Russell, Marvin Minsky, and Nick Bostrom who would argue that the Test is essentially worthless and is a distraction from the real work of AI. The only people actually working on passing the Turing Test are doing so as a hobby (eg. Ex Machina).

Minsky called one Turing competition “obnoxious and stupid” and even put up his own prize to shut it down.

Passing the Test was not meant as the goal of AI, but as a thought experiment to incite people who were skeptical of intelligent machines, or to prove that they could be intelligent through their behaviour and being indistinguishable from humans, not by being self-aware.

The players in our AI future, or rather machine learning, program-as-hardware, are likely to be the big guns: Google, Amazon (Lab126), Microsoft, IBM, and maybe even Andy Rubin’s new venture Playground. These are not hobbyists. There are different motivations. They are here to create value from machine learning for industry and for consumers. I’m particularly excited for the niche, consumer, mainstream market, every-single-day AI bots, like the expanding Slack bots (you spend your whole day in there anyways), Messenger (slowly usurping all your social chatting), and Fin (new contender from Sam Lessin and Andrew Kortina). These are not just cocktail party tricks.

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22 Mar Manual grind and AeroPress your best coffee

via The Noble List: “Discerning and functional things”


Still think making a great coffee is best left to the barista and their expensive coffee gear? Well, this combo of ceramic manual grinder and AeroPress is gonna prove you wrong, that you can make it yourself at home, or even take this compact gear with you on the road. Great coffee always starts with fresh, unground beans. Throw them into the $47.50 Porlex JP-30 Stainless Steel Coffee Grinder, and while your water is boiling, apply some elbow grease and burr those beans to fine shreds. (A decent powered grinder will start at $150.) Drop them into the $25.95 AeroPress Coffee and Espresso Maker, pour hot water into the top of the chamber, stir, and gently press the plunger for 30 seconds. Enjoy as your coffee has just been upgraded.

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24 Apr Legendary Harry Parker and 7 lessons for life

The legendary Harry Parker’s right hand man for many years, Bill Manning, recently penned this post “How Harry Trained Harvard.”

No other college rowing coach has had greater influence—or greater success—than the late Harry Parker. This is why.

Harry was head coach of Harvard rowing from 1963 until his passing in 2013. He has inspired fast rowers and, beyond, great leaders and successes. Many have tried to distill what he does into words, but I don’t think anyone has done it as well as Bill has just done. Here, in Bill’s powerful words, but in my summary, are seven lessons for anyone, not just rowers — for life, for leading a team, for your career, for excellence:

1. Rarely did he verbalize his expectations for his athletes: he wouldn’t limit his athletes by imposing expectations on them
2. Bigger challenges lie ahead: Harry would compliment a crew following a loss, but after a victory, however, he would more often motor off
3.Live up to tradition: but do so by focusing on simply doing the work rather than worrying about the outcome
4.Create a flexible and inclusive program for all levels of ability: allow others to find rowing just as meaningful and enjoyable
5.Boating even lineups, not race lineups, for training: a competitive environment fosters improvement, and everyone was accountable in every competitive situation
6.Outlast your opponents: Harry favored endurance training to sprinting. Sprinting is for the gifted, endurance is for those with character and inner fortitude
7.Positive psychological preparation: decide ahead of time that you will not be out-pulled.

Harry’s training had prepared them to race.

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20 Apr The state of in-car UX: it’s getting worse, and more technology is not the fix. Voice is.

Geoff Teehan of Toronto’s exquisite design firm Teehan+Lax recently posted on “The State of In-Car UX.”

It’s wonderfully visual and a worthwhile read, but still if you want a tldr: Teehan argues that no matter the price or the brand, the interfaces that adorn today’s vehicles are in a bad place. And they’re getting worse. Thankfully, there’s hope. Hope coming from Apple and Google.

Remember this? 1995 Nissan Pathfinder with aftermarket stereo:

Nissan Pathfinder

1995 Nissan Pathfinder

Now, for $845,000 in the otherwise luscious Porsche 918 Spyder, you get this. Really?

Big and obtrusive and distracting.

Big and obtrusive and distracting.

Is this really the UI people are raving about in the Tesla Model S?

Tesla S: still too much going on visually

Tesla S: still too much going on visually

Pretty galling especially to see Lambo and Ferrari electronics UI.

And in a $1.5M Lamborghini Reventon — what does it all mean? And that it often gets worse as the car gets more expensive.

Lamborghini Reventon -- what does it all mean?

Lamborghini Reventon — what does it all mean?

Jalopnik chimed in this week in “This Is The Worst New Trend In Car Interior Design

While touring the cars on display at the New York Auto Show, I was struck by how many of them get the integration of a screen into the dash right and how many of them get it wrong. If the screen is going to be a part of the car, shouldn’t it be integrated seamlessly into the design of the dash, rather than plastered on like a cheap Garmin you bought at Walmart?

An afterthought design earsore?

An afterthought design earsore?

The argument here is that: it’s only getting worse. The bright effort to slide your (familiar, better designed, fully functioning) iPad Mini onto the dash never seemed to have too much uptake. Car companies don’t hire or use people who design software for a living to conceive of and build the UX. Stereos, climate control, etc are designed either by industrial designers, car designers, or Human Machine Interface, which is what the car industry calls the people who deal with knobs and dials.

What’s next? Teehan harks on the arrival of Google and Apple CarPlay. Apparently, these software plus hardware giants are the panacea. And their placement of the buttons on the touch screens will solve our woes. While it seems reassuring at first, this is really no improvement.

I actually think this upcoming entrance of better software (via Google and Apple) into car UX is only a temporary stop-gap. In 10-15 years, cars (nicer cars) will (should) have super simple and many less controls. Like how Audi puts climate controls directly on the vents.

Control built into function

Audi: Control built into function

Your interactions will be all via voice and basic Head-up Display. HUDWAY reflects a simple UI from your phone onto the windshield. Here’s your inspiration:


Clean HUD concept from HUDWAY

So, without all the clutter of current software offerings, the (better car) interiors will be back to classic, no frills looks — like my dream Porsche 356, beautifully simple and minimalist:

Porsche 356

Porsche 356 cockpit; beautifully simple and minimalist

Summary: it’s easy to get caught up software-ifying the world and everything. Sometimes, especially when doing dangerous things like driving, the less interaction and the less design the better. The solution is not the smart and brash Apple and Google swooping in to fix the issue. The solution is voice-activated control, and maybe even HUD (Head-up Display) for navigation, and focusing on the driving part. At least until we’re all in driverless cars — 25 years away?

Dan Reitman chimes in with this great rant:

Colin Chapman, founder of Lotus cars, famously said “Simplify, then add lightness.” Of course, he probably didn’t consider Moore’s law, nor The Law Of 7-11 (Thine steed shall contain a cup-holder big enough to hold a Big Gulp). Cars would invariably get heavier and more complicated. This did not make for a better, safer driver – which should be the priority – nor does what Teehan is proposing.

He talks a lot about design purity and aesthetic beauty. He is an expert. Unless I missed it, he doesn’t, however, talk about ergonomics – and I wonder if he knows anything about them. To wit: how is a more pleasing font in a Porsche 918 infotainment screen going to improve my lap time or keep me from making sweet, violent, carbon-fibre love to a telephone pole at 100mph?

When I’m barrelling down the highway, I give precisely zero fucks about the fonts on my stereo screen. I care about how well I can feel around for the A/C controls (3 physical dials FTW, touchscreen = FAIL) or the volume knob, and where the flappy paddles are.

Teehan may like cars, but I bet you he’s just like the rest of the world’s distracted drivers: clogging the left lane while fiddling with his smartphone. The fact that he thinks any kind of swipe gesture is a remotely sound ergonomic choice for a car hammers this home.

This leads to a bigger issue about how we use our cars. I get that driving habits are, of course, a regional thing. I was just in LA for a couple of days and was reminded how bad the traffic was there – Jeff, i am guessing the Bay Area is just as bad. California is also, of course, a massive car market. If i lived in those places and had a commute that regularly involved me stuck in crawling traffic, I would likely be interested in things like in-car internet and other infotainment options that were optimized – both aesthetically and functionally – for my use, as Teehan describes.

The other side of the coin is those who believe that driving, whether on the Autobahn or in a gridlock traffic, is an activity that should involve minimal distraction and interference from other pursuits. Drivers should be focused on moving as quickly and safely as possible (and stay the out of the left lane) until they reach their destination, at which point they can start surfing the web or doing whatever else they need to do. Drivers in Europe seem to have this one figured out pretty well.

TL; DR – Teehan is barking up the wrong tree, IMHO. He’s pushing for improving in-car UX as it applies to infotainment – but the car is not yet an appliance; those things are secondary, and if they aren’t treated as such, we’re just going to have more distracted drivers who are a nuisance and hazard on public roads. Build me an interior that focuses on driver alertness, safety, and comfort – in that order – and worry about turning your car into a Bang & Olufsen or Apple showroom when the thing is parked.

Less and smarter technology, more voice activated features. Less distraction, more safe driving. Less buttons, more classic clean design. What are your favourite car interiors free of design clutter?

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06 Mar Time to panic Canada. In 32 days, your fate #Quebec2014

Just 18 months since gaining a minority leadership, Quebec’s separatist premier Pauline Marois has called a snap election within 33 days. Tick tock. From today, 32 days to go.

Let’s not be vague about this.

If you live in Quebec, please don’t even think about missing this vote. Here are two reasons, for example, not to vote for Marois’ Parti Québécois government:

1) Their secular charter: a proposed law that would ban the wearing of overt religious symbols by any government employee or by workers at institutions. Really?

2) Separatism. This might have been fathomable 20+ years ago, but now Quebec is far from Canada’s economic engine. Today, Alberta is in the driver’s seat, as Quebec dawdles with its bloated welfare, dysfunctional infrastructure programs, impotent energy resource development, and absurd language laws repelling investors. More below.

Actually, no matter for whom you vote, don’t miss this one.

If you can’t vote in Quebec, but are Canadian, let’s consider separatism again:

1) PQ wins majority = likely. They are ahead in the polls. Also, the opposition’s new leader, Philippe Couillard, is generally seen as a weak leader, even by some of his own Liberal party members.

2) PQ calls a referendum to secede from Canada = likely

3) Referendum squeaks by and passes by 50%+1 = likely

4) Quebec secedes from Canada = likely

5) Canada cannot withstand a truncated geography and crumbles = likely

6) No more Canada, one of this past century’s greatest nations

I’m no political scientist. I don’t even live in Quebec anymore. There’s a lot about this election that I don’t understand. But here are two things everyone should be doing for 32 days:

1) Vote if you can

2) Visibly show your love for Canada and Quebec

I love Montreal and Quebec and Canada. Thanks. Please panic now and do your part.

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26 Feb Wins and losses from #sochi2014 and lessons for future Olympic Games

I continue my love – hate with the Olympics. The Games in Sochi just came to a close, and while they were full of horrifying politics, pathetic media coverage, and IOC bureaucracy, they were also full of incredible human triumphs through sport, by these incredible athletes.

The world, connectivity, and significance of these athletes as role models are changing quickly, so I’m hoping those who are part of crafting such an important amateur sports event will consider how to stay relevant in the Games to come. My thoughts on the winners and losers and lessons:


LOSER: Big media for spoiling the results. News, apps, scrollers, and TV felt they had to be the first to announce winners (and disappointments of course), and considering the time change from Sochi to North America, didn’t seem to care that some people sometimes enjoy watching sport without knowing the outcome. Consider that many events were broadcast time-delayed, this was so painful. NBC.com even titled their online videos with the result.

WINNER: CBC for broadcasting on-demand streams (often live) of all of the events, without titling the video with the outcome.


LOSER: Judged sports. There were no loss of controversy over who won and who didn’t in judged sports, from freestyle skiing to, worse, figure skating. There was no shortage of fuming about Russia’s own Adelina Sotnikova “stealing” the gold from favourite and defending Olympic champ Yuna Kim of South Korea. Lesson: if you can’t stand the uncertainty of judged sports, don’t play them; enter a race. Otherwise, realize how part of your fate is decided by other people’s opinions, tastes, and maybe even wallets.

Sotnikova Kim

WINNER: Snowboarders who put into perspective the realities of judged sports, like bronze medal, easy-going, Canadian snowboarder Mark McMorris, “but it’s a judged sport, what can you do?

It’s easy when you’re the gold medalist to be the one to put it in perspective, but you gotta love Sage Kotsenburg’s interview on Conan:


LOSER: NBC focusing on American athletes only during coverage. They would often skip an A Final in favour of showing the B Final with the American, or only report on the America’s result, not even the medalists.

WINNER: NBC improving by doing some great profiles on international star athletes, nearly making them heroes to Americans. NHL Revealed will even broadcast “NHL Revealed has two-hour behind the scenes special on Olympic hockey tonight” — I hope for Rio 2016, media with access could do the same for other sports, and build up personalities, history, and rivalries weeks maybe before the events take place. I can only think this would bolster their viewing interest.


LOSER: Russia and its $50B wasted. The glorification of the Putin Games did manage to gloss over the travesties of lack of human rights, burning Ukraine, and corrupt $50B spending during the Games. Media became pretty quiet on calling Russia and Putin out.

WINNER: Safety of athletes and fans. It’s almost hard to believe with all that friction and animosity, that no tragic incident took place in Sochi. Amen.


LOSER: Legacy of the Games. The new world-class facilities built for the Games will likely be wasted, or shut down, or moved, and will likely not help future athletes in their pursuit of excellence. Shame.

WINNER: Conan’s “Sochi’s PR Rep Says Everything Is Going Great”


LOSER: Too much figure skating on TV. And their ridiculously over-thought and over-sparkly outfits and haircut strategies. Is TV changing their approach to the viewing demographic? Do women watch TV and men watch streaming video online?

WINNER: Hero athletes, i.e. cross country skiing heroes. These incredible men and women push themselves so hard, right to the finish line, to their absolute limit, and cannot even stand after crossing the line. True heroes for grit and determination. Wow.



LOSER: NBC presenting their coverage as if it’s reality TV! Great read from Slate: “Why You Hate NBC’s Olympics Coverage: It’s reality TV masquerading as a sporting event.”

WINNER: The real, often overlooking stories of the athletes. I was watching the men’s slalom, and way, way back in the results and start list was this guy: Hubertus von hohenlohe, the one man Mexican Olympic team. He is also… a German prince, 55 years old, a world-class photographer, a professional musician, fluent in five languages, and an heir to an automobile fortune. And participating in his fifth Olympics. Despite his fortunate upbringing, he is valiantly trying to bring attention in Mexico to Olympic sport. In his mariachi suit, however, he was struggling, 17 seconds back of the winner. (NBC video)



WINNER: Bringing back Canadian former Olympians as commentators: Jenn Heil, Ashleigh McIvor, Adam van Koeverden, Kelly VanderBeek, Clara Hughes, Beckie Scott, Kristina Groves, Jennifer Botterill, Kerrin Lee-Gartner, etc. Nearly every event had a former great in the second seat calling it for TV. This was incredible not just giving an insider look, or even appropriately lionizing our Canadian heroes, but also giving them exposure to this world and a potential for some future work in media, for people who had dedicated so much, and often had to neglect their career in the past to pursue that level of sport.

WINNER: Canadians acting like champions. Canada had no reason to apologize and confirm to our “I’m Sorry” stereotype. They crushed it. Nice job.


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23 Aug 3 things everyone needs to do better

Come on. It’s 2013. Learn to deal with the world and people around you.

1) How to take a decent photo. Step one: aim. Is your subject in the frame? Have you looked at your four edges that they don’t cut off their feet or head? Do you have a big massive space of nothing for no good reason? Move with your legs to a better spot, and fix it. Step two: on a camera, press the shutter halfway, let the camera focus, then when you’re ready press the rest of the way. No more shutter jabs! On a touchscreen / mobile phone, press and hold the shutter, and when it’s good, release to shoot. Step three: only use zoom if moving the position of your camera doesn’t do what you want. I mean use your legs and walk. Zoom doesn’t just move you closer, it’s changes a lot more. Save that lesson for later.

Bad Photography Example 6

2) Grammar. There is no excuse to confuse “it’s” and “its” or “there” and “their” and “they’re” or “your” and “you’re.” Take 5 minutes, and teach yourself.

3) Don’t get on an elevator if people are still getting off.

Now we’ll all get along. Thanks for reading.

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23 Aug The contentious Bill O’Reilly with sound life advice

“You don’t rely on anybody. You make your way. And you’re gonna get slapped down. And that’s okay. You get back up. Sometimes you’re gonna succeed, sometimes you’re gonna fail. But somebody pays you a wage — you go in, you do the best job you can, and you take your pay home. You don’t like the job, you get another job. But that’s what I want people to be: I want them to use their talent to be self-reliant, to be honest, to give to charity, to be fair — all of those things.” –Bill O’Reilly on Q with Jian Ghomeshi

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