Week 7 - Techstars NYC

Week 7 - Techstars NYC

The Elevator Pitch

Week 7 kicked off the final stretch of the program, during which we would normally be preparing for Demo Day.  There have been a few posts written recently (Ty Danco, Ross Baird)  about why we should be changing Demo Days, and Techstars NYC has been experimenting with a different format.

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Lean Systems - My Next Project

Lean Systems - My Next Project

New Startup!

I've joined a new startup called Lean Systems (as of September)!  I'm super excited about the project, in which I'm now a cofounder, and the last few months since joining have been awesome.  I wanted to share a bit about the company, as well as my thought process in selecting a new challenge following my time as an Associate with Techstars Boston (Spring 2016).

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Techstars Boston Week 11 - Last Workshop

Techstars Boston Week 11 - Last Workshop

This week was the last "normal" week in Techstars, before the pitch practice madness begins.  The final week was full of workshops, with the last workshop on Friday, and the topics varied from selling techniques, to common VC (venture capital) pitch mistakes, to PR (public relations) strategy.

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Techstars Boston Week 10 - Acquisition

Techstars Boston Week 10 - Acquisition

Customer acquisition is usually the foremost topic on a founder's mind.  This week was full of workshops, focused on various aspects of this topic. We also heard one of the most powerful Founder Stories of the program.

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Techstars Boston Week 9 - Product

Techstars Boston Week 9 - Product

After dipping briefly following Mentor Madness (at least in feel), the pace here has started to noticeably increase again.  That mostly means founders and teams have less time for distractions, and are putting in even longer hours than usual.  New product is being shipped, and more time is being dedicated to fundraising and sales, in preparation for Demo Day. As such, the focus this week was mostly on product development, and putting more pressure on growth.

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Techstars Boston Week 8 - Enterprise

Techstars Boston Week 8 - Enterprise

For whatever reason, this week the workshops focused largely on enterprise-oriented companies, and the Founder Stories happened to come from two people involved with an enterprise-focused company. From a general standpoint, this week has been about growth.  Companies are spending a lot of time working out their strategy for the next 6-12 months, and which direction they will head after Techstars.

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VC Pitch Tips for the Lazy


Phil Libin has been tweeting VC pitch tips that are pure gold the last few months, and given we're coming up to Demo Day here at Techstars Boston (May 25, you're invited!), it seemed a particularly good time to highlight some of the best. This post is modeled on one from Stelios Constantinides called Paul Graham's Startup Advice for the Lazy, and curated with a Demo Day presentation in mind.

Get the full list of VC Pitch Tips, including those aimed at fundraising and general startup tips here.

Demo Day VC Pitch Tips:

  • Why this? Why you? Why now?
  • Label your axes.
  • When you're practicing the presentation in your head and you think you might apologize for some part of it, fix it instead.
  • Put aside financial interest and describe what the world looks like if your startup is successful. Make us want to live there.
  • Use your company name and logo intentionally and only when you want to have an impact. Don't waste them on your slide masters.
  • It's ok to be nervous and awkward. We're looking for authenticity, originality, energy, infatuation and mastery; not polish.
  • You won't get credit for hedging your bets; that's why we have portfolios. Build your startup around a sharp point of view.
  • Don't read your slides.
  • Even if this is the hundredth time, try to remember what you felt like the first time you pitched this idea. Do it like that.
  • Humility > bragging > false humility.
  • Clouds of random logos; whether customers, competitors, partners or previous experience; are not effective slides. Rethink.
  • Try this: delete all logos, clip art and bullets from your deck. What's left is what VCs actually remember. Is it good enough?
  • Retention better than growth as early predictor of startup success because it's less effected by hype. Engagement is 2nd best.
  • Finish early.
  • Bullet points often mask incoherent trains of thought. Rewrite as complete sentences t see where you're fooling yourself.
  • Don't rely on partnerships to reach your early adopters. Maybe a good way to scale, but a bad way to start. Do it yourself.
  • Try not to violate more than one long-established, conventional wisdom, unquestioned truth at a time. Or less than one.
  • Unless you really, really know what you're doing, please stay away from the font menu.
  • Speak at your normal pace. If you find yourself struggling to get through the deck on time, cut slides. Better than rushing.
  • These are words you don't need to use anymore: "SaaS", "Cloud", "Mobile". "Blockchain" is borderline.
  • It's really weird to add up the years of experience of each member of your startup team and present it as a single number.
  • If you get knocked off your script, don't rush to get back to the slides; good opportunity to show you really know the problem.
  • Be rigorously optimistic: Believe that the world will get better. Know that it’s your job to improve it. Have a plan to do so.
  • This should go without saying, but please don't trash talk your customers... You know what? Go ahead. Makes my job easier.
  • Hide the bullet marks from a slide. Look stupid? You wrote some jargo-gibberish and the dots were tricking your brain. Rewrite.
  • Quick bursts from external events, like an AppStore promo, are great, but evidence of sustained growth is much more persuasive.
  • Great products aren't neutral. They have a strong point of view inextricably tied to every design decision.
  • Make sure your CAC ain't whack, yo.
  • Eschew industry jargon, even when everyone else babbles it. It doesn't show mastery and it makes you blend in, not stand out.
  • Anonymous customer testimonials feel dishonest. Ask for permission to use real names or omit.
  • Products that help people do something good are generally more interesting than ones that try to prevent something bad.
  • You don't have to open with a joke.
  • When measuring retention, try to eliminate early noise. Something like: what % of week 2 users are still active in week 4?
  • For just about any metric, an improving trend is more interesting, and predictive of long term success, than a single point.
  • Every slide you show dilutes the impact of every other slide. Keep this in mind when deciding what to include in your deck.
  • If you're going to list advisors on your team slide, be prepared to talk about what advice they're giving you.
  • The world probably doesn't need more ads. Smarter, better, fewer: sure.
  • Design your deck with the right empathy point: optimize for the experience of the audience, not the comfort of the presenter.
  • Don't fetishize "disruption"; it's a side-effect of successful innovation, not the goal. Focus on creating big new value.
  • Don't worry about raising too much; you won't regret more cash in the bank, even with dilution. Worry about spending too much.

Don't forget to check out the full 7-page PDF list of VC Pitch Tips from Phil Libin here.

Happy pitching!

Techstars Boston Week 7 - Fundraising


While I didn't get to reflect on Techstars during the last couple weeks as much as I would have liked, given that I was traveling back to Montreal and Nova Scotia on the weekends, last week was yet another week full of learning. And while the title of this post is Fundraising, we aren't really there yet.  But the workshops at Techstars were focused here this week, and they were so good they deserved the title.

We had fewer sponsors this week, which let all of us (including Associates) really get into our work, and we had another couple great workshops and Founder Stories.

Techstars Workshops

Cap Tables

This workshop, while perhaps not the most interesting of topics, was very useful.  The workshop focused on modeling different investment and cap table scenarios and the resulting equity distributions.  The bottom lines:

  • You need to understand in detail all the implications all term sheets you consider, including the future consequences with your likely fundraising milestones.
  • Beware taking a lot of convertible notes - this can kill you down the road.
  • Pre-money vs. post-money has major implications for every deal you do, but make sure you know all the different situations it applies, as they're often wider than most people think.
  • The combination of employee equity pools, equity guarantees (for things like accelerators), and high amounts of capped convertible debt can spell disaster for founders, so make sure you don't end up in this situation.
  • The investors you're dealing with have done this a hundred times; get a mentor and/or lawyer who is equal to the task and has your best interests in mind.

The bottom line here is that with a few small mistakes in interpretation, you can end up with very little equity.  Don't take fundraising of any kind trivially.


This workshop was given by David Cohen, and was the single best resource I've ever been exposed to on closing an investor.  I'm still trying to find some public resources to share since it's so good, but for now here are some tips (keep in mind this is based on Techstars companies only):

  • You should have an amount of money to raise as your target (call it 'T'), and should 'know' that you can exceed this target.  In other words, the overask is the killer in fundraising.
  • If you have a demo day coming up, you should be aiming to have at least 1/3 of T committed going in.
  • Ask investors you have developed relationship with to "help you" by committing early.
    • Don't ask them to lead, just to commit.
    • Make it safe for them to commit (ie. no cheque required).
  • "Soft commit": agreement to invest specific amount of money with specific, well understood conditions.
    • Example of one condition: "I can't commit without the valuation." "Will you commit, assuming the valuation is ultimately acceptable to you?" - provide the "out".
  • Practice active listening to get to commitment.
    • LISTEN.
    • Your job is to remove concern, not solve it.
    • Once condition is mentioned, write it down, repeat, ask if you got it right, ask what else.
    • Your goal is an exhaustive list of conditions under which they will invest.
  • Ask clearly for the commitment at the end:
    • "So, assuming [condition 1], [condition 2], [condition 3] are met, I understand you are willing to commit $[___]."
    • Ask if you can use their name when talking with other investors.
  • Enjoy having your lead investor!

Okay, so it's not quite that simple.  But the active listening, and removing concerns was a huge revelation for me.  Everyone will tell you that once you have a lead investor, things become considerably easier, as investors like to invest with others, but this is the best methodology I've ever seen for getting the soft commit you need to get other investors on board.  Enjoy!

Founder Story

While the details of this story, as with all Founder Stories, are kept among those who are present when they are told, this was one of the more amazing stories.  Tom Leighton from Akamai, a company which has been through a bunch of ups and downs on all sides of the business, from the valuation to the leadership, shared his story with us, and some of the most amazing takeaways I got were based on Tom himself:

  • Being humble, kind, and extremely successful are not mutually exclusive.  To the contrary, I think that a disproportionate number of great entrepreneurs are good people, and Tom is a great example of that.
  • Leadership and the ability to be a CEO can be learned; the caveat is that it might take time.  Tom himself was with the company for many years before stepping into the role.
  • Culture and hiring is extremely important to the company; on the topic of navigating crisis, breaking bad news, or other general obstacles for the ups and downs of a startup company are often a non-issue when you have a great team made of great people.
  • You have to be lucky to be good, and good to be lucky.  This old cliché holds true for most aspects of life - but you need to always be positioned to take advantage of opportunities that come your way.  Often they can be the break you need to get ahead, or to keep the company alive period.

If you're more interested in the story, check out this book:

Airplanes & Productivity

I flew home this past weekend for a funeral, which while obviously a sad occasion, provided me some much-needed reading time during my flights.  I was once again reminded how valuable carving out undisturbed time to read and learn can be.  During one ninety-minute flight, and the last three quarters of a book (Traction, in this case), I had the best ideation session of the past several weeks (maybe even months), and no doubt it was the lack of distractions aside from my book, notepad and pen.

Whenever you can, make sure to escape somewhere to take some time to read and think.  And don't just hope it happens - schedule it in your day.

The books I finished recently:

Until next week!

Techstars Boston Week 6 - Hangover


This week at Techstars finally marked the end of Mentor Madness (hence the Mentor Madness hangover), and it was a relief for many teams.  I don't think I've seen the office quieter, or more productive, than Monday, the first day without scheduled mentor meetings.  That said, teams continue to meet with mentors they liked, some often for their fourth or fifth meetings. The Founder Stories and Workshops this week provided some brilliant content, which you can read about below.

Techstars Sponsor Visits

Though the formal Mentor Madness period ended, sponsors began sending their startup teams, and the personnel on these teams also fit the mentor role.  Many have backgrounds in either starting companies or funding them via venture capital, and their experience shows.

While sometimes visiting with sponsors is optional, I've personally seen it be extremely valuable for more than one team over the past several weeks, and I would recommend always visiting with sponsors if given the chance.

The reason: some will be non-technical while others will be technical, meaning you can send different people, and typically only one or two sponsors visit at a time, meaning that you will likely only have half an hour of your day occupied.  Based on the opportunities and connections many can offer (think customer introductions, hugely valuable perks, investor introductions), the potential for return is high for the time committed.

Founder Stories

This week, in addition to the usual Founder Stories from within Techstars, we had a special guest courtesy of a sponsor, from a local startup.

While the industry wasn't one I was generally familiar with, there were some great takeaways:

  • As a founder, you have to make progress every day.
  • Raising a seed round is based on any one of three things: product, team and traction.
  • Traction has a wide scope - things like customer interviews count.
  • Seed fundraising mistakes: talking to big VC firms.
    • Instead, talk to large angels.
  • To get your valuation for your seed round, talk to people who have done similar size seed rounds recently.
  • Getting investment from people you actually like should be a high priority - if investor meetings go badly, think about whether it's because of the person.
  • Set personal meetings (like lunch) with investors to first check the fit, and make that one of the early interactions before you approach fundraising with that person.

Our own Founder Stories tend to be more personal, and this week was no exception.  We had two very different perspectives and styles of stories, so I've broken the lessons from each in two:

From the first:

  • Most obstacles just really aren't that big; whether it's moving countries, changing locations because of someone you love, or someone you've lost, it's all possible.
  • The corollary to the above is that most obstacles we see are self-imposed.  The barrier to accomplishing something is often within ourselves and the perceived obstacles, rather than reality.
  • Businesses that are a result of your past, and/or tied strongly to your own life, are often the most powerful.
  • The corollary here is that when telling the story of your business, it is much easier to make an emotional connection when the story is your own.
  • Your story can be a recruiting tool.  If you've experienced it, others likely have to; who are these people and how do you find them?

From the second:

  • Switching study or career paths isn't something you should be afraid of.
  • When thinking about which areas interest you, consider your interests outside of formal study - how can they be tied to formal studies or careers?
  • Getting funded by your parents, living at home, and doing whatever you can to make your business succeed, is okay (personally, this resonated a lot for me).
  • Great products take a long time to develop.
  • The path to product/market fit is often a long one.
  • Cofounder relationships are precious, and like real relationships, can be ugly when they finish; make sure to think and proceed carefully when considering who you found with.


Behavioral Interviewing

This workshop forever changed the way I will conduct hiring.

The highlights:

  • Gut instinct is only good for those who you shouldn't hire.
  • The best predictor for success is previous behavior, NOT previous experience.
  • "The average hard & productivity costs of a bad hire is 15x base salary" - Who, Geoff Smart & Randy Street
  • You need a scorecard for hiring based on three things: behaviors, competencies, and outcomes. Hire for what you want the person to accomplish in THIS job, at THIS time.
  • For behaviors, always ask "Tell me about a time in your career when you _____".
  • Six behavioral essentials: grit, rigor, impact, teamwork, ownership, curiosity, polish.
  • Competencies: technical, cultural.
  • Outcomes: 3-8 specific examples of what a person must get done.
  • CEOs: you are full-time recruiters.  You should always be asking other people who they think is talented, and start relationships with these people.
  • Selection process: filter [resumes], screen [with a call], interview [with multiple teams, for several hours], decide, reference.
  • Use TORQ (Threat of a Reference Check) in questions (ie. "When I ask your old boss about ___, what would they say about ____").
  • Look for STAR answers (Situation or Task, Action taken, Result).
  • You should be listening more than talking during most of the interview (the end is for selling your company).
  • A key interview might take 90+ minutes; make use of the scale and grade people.
  • You should have multiple interview teams; only ask references once you've decided to hire.
  • As usual: hire slow, fire fast.


Again, this was a transformative workshop; everyone here will probably hire like this for the rest of their careers.

Exploring Cofounder Conflict & Being Fierce

While this didn't provide the crazy mind shift that the first workshop did, it explored some issues that often aren't in entrepreneurship, mostly on the topic of emotional stability and overall happiness.  The following were the main points for me:

  • In general, make an effort to ask your cofounder(s) and coworkers "How are you?" and truly listen to the answer.  Schedule a meeting if necessary. You should be looking to find out where they are in their personal and work life.  Use a red/yellow/green scale if need be, and it's up to the person whether they elaborate.
  • If you have an issue, use ONFR: Observation, Feeling, Need, Request:
    • O: I noticed _______.
    • F: That makes me feel ______.
    • N: We need to agree on ______.
    • R: Next time please ______.
  • Try and get your whole team asking themselves the following, as they relate to both their work and personal lives:
    • What are you not saying that needs to be said?
    • What are you not hearing that's being said?
    • What are you saying that's not being heard?

Emotional and overall stability is key for a person or team to function long-term.  There is often a particularly masochistic culture in entrepreneurship as it relates to work-life balance, or whatever you like to call it.  Regardless of the balance, make sure you know where both you and your team are on these issues.


The focus this week is definitely shifting.  Despite still being busy with sponsor visits and events, there has clearly been a move back towards fast progress, and it will be fun to watch (and participate in) over the next few weeks.  This also marked the end of the first half of the program.  I expect the second half to be much different, though no less interesting.


Techstars Boston Week 4 - Efficiency


If you haven't read any of the previous posts, start with my post about Techstars Week 1. Efficiency was the key in Techstars last week, and with that in mind, I'm going to make this post mostly in bullet points.

Mentor Madness continued last week, though everyone was starting to try and reduce the number of meetings to key personalities, and investors starting making their rounds.

Sales is Still King for Techstars Companies

This point was hammered home yet again, throughout the week.  Not only does sales actually involve a lot of things - customer interviews, verbalizing and articulating your value proposition and benefits, convincing customers to buy, and actually closing - but it's the true determinant of product/market fit, investment readiness, and a host of other good things.

In essence, if you can prove some sales success, a lot of other things will become much easier.  Financing, hiring...you get the gist.  And more often than not, teams are still getting their heads around the fact that they are ready to increase their sales volume, and don't require more product development or hiring, or other things on their priority list.  They just need to sell.  It will probably take some more time before it really hits home with everyone.

Techstars companies in general are a little closer to product/market fit than a lot of startups, but the lesson is that you're probably ready to sell before you think you are.

Closing is a Skill

We had a great closing workshop (provided internally by a Techstars participant) this week that lasted all of 20 minutes.  Seriously.  And the end result is a clear, repeatable strategy that can be deployed by anyone who is reasonably persistent, knows your product and value proposition, and is willing to practice.  The notes from that workshop:

  • You want to be "solution-oriented expert" - not salesperson.
    • You listen to the problems of the customer.
    • Only go over features that are relevant to them - you need to be able to link features to pain points.
    • They have to see the value - cost savings or benefit outweighing cost.
  • Time to close: talk about pricing, ask for the close - "are you going to pay with Visa, Mastercard, American Express?".
    • Next step: shut up; need to give them time to process.
    • First one to talk loses (within reason).
  • Be prepared for objections; prepare a list of objections and rebuttals beforehand.
    • Try and address these early in the call (ex. ask early if there is anyone else you need on the call to make the decision).
    • Don't offer extra rebuttals - they may have more objections.
    • Know your competition so you know why you're better.
    • You have to hold their hand and lead them through the process.
    • Outline all steps to buying for them.
  • If rejected, make sure to ask "is there anything I could have done to get your business?" - learn from the rejection.
  • If they say they need to check with someone, ask "are there any problems you can foresee?" - always get as much information as possible.
  • Use "second voicing" - pretend your manager is next to you when you check on discounts, other options, etc.
  • Create urgency - limited time price offer, cap on number of customers, etc.
  • Use social proof - show them reviews and testimonials.
  • Use the feel, felt, found technique: "I understand how you feel, lots of others have felt that way, what we have found is when app is used it's easy, and we have a great support system".
  • Make sure if you don't close, they have an action item for the next step.

The only thing that needs to change between sales jobs is knowing the industry and the product.

Extra Resources

Close.io Blog (particularly Steli Efti's writing)

Predictable Revenue - Aaron Ross & Marylou Tyler

Founder Story Insight

This week was an external founder, a former Techstars alumni, who came in to share their insights.  As usual, it was a brilliant story, and there was lots of great anecdotes.  In keeping with the efficiency theme of this post:

  • Talk to customers.
  • Celebrate all the small victories.
  • If you're building a company, you need to go all-in - no distractions.
  • Go where your customers are to build your company.
  • Mentor sessions - ask lots of questions, then be ruthless, and pick 3 or 4 to build deep relationships with.
  • Raise money when you can, not when you need to.
  • Raise from people who want you to succeed as a CEO.
  • Team is important, but they are always second to the customer;
    • Never hire people you wouldn't want at your birthday party.
    • Your job will become miserable the moment you break this rule.
    • Hire people smarter than yourself and who have more experience than yourself.
    • Hire people who inspire you to overcome the shitty days.
  • Enjoy the journey.
  • A personal connection with your investor(s) is critical.
  • There is a big difference between being stubborn as a founder, versus a lack of self-awareness, and this will scare off VCs if not managed.
  • In choosing between customer segments: How big is the pain? How easy is it to sell? How many people are there? Do they have money?

Growth Hacking

This week also marked an interesting week in chatting about "growth hacking" techniques with both mentors and companies.  For those who don't know what growth hacking is, here's a good resource to learn more.  I'll be posting more about this in the coming weeks, as I do some work with companies on this topic.

Until next week!