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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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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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 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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