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 5 - Madness Over!


This was the last week of Mentor Madness at Techstars Boston, and for the most part, everyone was breathing a sigh of relief.  Usually investors are the last ones to participate, so despite being near the end, you still have to on your game. That also meant that Workshops began; Workshops are often lead by mentors on topics in their area of expertise, and generally follow the focus of the program: Build Team, Build Product, Growth.

This week we had two:

  1. Customer Interviewing: this was a detailed presentation of how to set up customer interviews, the right questions to ask, and the questions to avoid, with an example interview done in the middle.  Super useful.
  2. The Power of the Network: a summary of how to leverage the Techstars network, and the associated tools, which include LinkedIn.  Again, super useful, and Techstars does a great job of utilizing their network in general.  While the opinions I've received on the topic are obviously biased, many would argue it's the most valuable network for entrepreneurs globally.

So, we'll start with those.

Customer Interviewing

I think this is probably one of the most overlooked skills in the entire of entrepreneurship.  Not only can customer interviews help chart your product development, sales strategy, and basically every consumer-related aspect of your business, but this is where you can find out if your startup idea is worth something in the first place.

The key takeaways:

  • Surveys can serve as validation tools, and that's about it.
  • Be as vague as possible to start - don't tell them what industry you're in, even remotely what your startup does.
  • Good interviewing is good listening - you want them to tell stories.
  • Stay away from 'shallow' (yes/no) questions.
  • Avoid "have you ever had ____ problem".
  • Always go for more "tell me about the challenges you've had with _____" (ex. note-taking).
  • Interviews should be conducted with two people, one who is clearly in charge and one who is taking notes - can enter conversation occasionally by asking "do you mind if I ask a question?".
  • You always want to dig deeper and get the stories; good follow-up questions include things like "why?" and "how often does this happen?".
  • Wait for the other person to speak and elaborate themselves - using silence is important.
  • Get people to demonstrate their stories and experiences if possible - you can then ask questions based on the demonstration.
  • Approach interview as "how can I disprove my core assumptions?" - don't be married to your value proposition.
  • Try and find the current way this person is solving your problem.
  • Can source interview people from Craigslist, Taskrabbit - you should be getting valuable information after 2 or 3 if you're doing it right, and you shouldn't have a problem filling more than 45 minutes.

Power of the Network - Techstars & Otherwise

While some of this workshop spoke about how to best leverage the Techstars network specifically, there was a lot to be gained from the LinkedIn and general networking advice:

  • Spend 10 minutes every day responding to points of contact (on LinkedIn) - congratulate people on new jobs, introduce them to someone you know in their new city, comment on their post, etc. (Go to My Network > Connections to see updates).
  • Publish blog posts on LinkedIn - particularly if you post elsewhere too; it's a great way to show off your skills to people, and to dictate your own specialties and positioning.
  • Little-used feature - you can keep notes that are private to you on first-level connections - just look at their profile and you'll see the option below their header.
  • Use Conspire to get introductions.  Look for lowest number of people in pathway, not necessarily strongest.
  • Go to My Network > Connections > Settings to integrate with other services.
  • University affiliation is a great way to turn a conversation from cold to warm, and is underutilized; check out the Advanced Search in detail.
  • Use My Network > Find Alumni to source talent, or VCs/investors.
  • Search former employees of a certain company to get intelligence and background information.
  • Look at who has viewed your profile - if you don't have the right people viewing it, change your profile.
  • Use your skill endorsements as a gauge for how other people view your skill set and expertise.
  • Look at who is the most-viewed in your network - they have the highest social influence and capital; utilize this.

Founder Stories

I won't say much about the Founder Stories this week, since they were so personal and emotional.  That being said, they did really drive home a few key points for me:

  • There is more to life than startups, or career success, or pretty much anything except family and loved ones.  Never lose perspective.
  • Desperation is a great motivator; use it as a tool (and by this, I mean implement it artificially whenever possible).
  • The arguments against immigrants in any country are stupid.  From an economic standpoint, they create disproportionate value.  Aside from that, see point 1 - these are all people seeking the same things as you are.
  • Obstacles are just that - obstacles.  And yours are probably much less daunting than many that many, many, other people have faced and overcome. In other words, if you think your life is hard, it probably isn't.
  • People are amazingly resilient.

I'll use the opportunity to point back to one of my favorite articles from Paul Graham, titled Life Is Short.

The end of Mentor Madness is a net positive for me, and I'll probably dedicate a separate post or two to the whole process.  In the meantime, you can refer to Deb McGargle's post about it.