YC Root Access

Lecture 19 - Sales and Marketing; How to Talk to Investors (Tyler Bosmeny; YC Partners)

Lecture Transcript: http://genius.com/Tyler-bosmeny-lecture-19-sales-and-marketing-how-to-pitch-and-investor-meeting-roleplaying-annotated Three segments in this lecture: Tyler Bosmeny, founder and CEO of Clever, starts off today's lecture with an overview of the Sales Funnel, and how to get to your first $1 Million. Michael Seibel, founder of Justin.tv and Socialcam and Partner at Y Combinator, then goes over how to talk to investors - the pitch. Dalton Caldwell, founder of imeem and App.net and Partner at Y Combiantor, and Qasar Younis, founder of Talkbin and Partner at Y Combinator, then perform an investor meeting roleplay to give you a taste of how it actually might look behind the scenes. See the slides and readings at startupclass.samaltman.com/courses/lec19/ Discuss this lecture: https://startupclass.co/courses/how-to-start-a-startup/lectures/64048 This video is under Creative Commons license: http://creativecommons.org/licenses/by-nc-nd/2.5/

Dec 2, 2014·48m·Watch on YouTube ↗

📖 CHAPTERS

1. 1

   Tyler Bosmeny’s path into sales and why founders must sell

   Tyler introduces himself as CEO of Clever and explains how he unexpectedly learned sales at an early-stage startup. He reframes sales as an essential founder responsibility, not something you “hire for later.”

2. 2

   The early-stage sales funnel: prospect → conversation → close

   Tyler lays out a practical early-stage sales funnel and previews tactics Clever used at each stage. The goal is to make sales concrete and executable for founders doing zero-to-one revenue.

3. 3

   Prospecting math: finding the 2.5% innovators who’ll buy from a startup

   He applies the technology adoption curve to show why early-stage selling is a numbers game. Only a small tail of the market will consider an unproven startup, so volume and persistence matter.

4. 4

   Three prospecting channels that worked: network, conferences, cold email

   Tyler describes the highest-leverage sources of early prospects, emphasizing conferences and well-executed cold outreach. He highlights tactics for making in-person events highly efficient.

5. 5

   Cold email template: short, direct, and easy to say yes to

   He shares a simple cold email structure that avoids long explanations. The emphasis is on brevity, clarity, and a specific near-term call to action.

6. 6

   Discovery calls: the #1 rule is to stop talking and ask questions

   Tyler’s central sales lesson is that founders should talk less and listen more. Great sales calls are mostly the customer speaking, with the seller guiding via questions.

7. 7

   Follow-up discipline: what closing really looks like (messy and repetitive)

   He demystifies closing by showing how many steps and touches it can take—even with an interested buyer. Founders must develop “unreasonable” follow-up habits while protecting their time.

8. 8

   Closing mechanics: redlining, standard contracts, and avoiding lawyer-driven stalls

   Tyler explains redlining and why contract negotiation shouldn’t become a startup-killer. He highlights YC’s move to open source standard deal documents to remove friction.

9. 9

   Three closing traps: “one more feature,” free trials, and losing the goal

   He warns about common endgame pitfalls that waste time and delay real commitment. The theme is trading vague interest for concrete agreements.

10. 10

    From unscalable to scalable sales: matching motion to pricing and customer count

    Tyler transitions from early hustle to thinking about repeatability. He explains how sales effort must align with pricing strategy and the type of business you’re building.

11. 11

    Why YC shifts to fundraising: build the company and pitching gets easier

    The session transitions to investor conversations, with a reminder that YC doesn’t overemphasize pitch polish. Strong traction and execution make fundraising smoother.

12. 12

    Michael Seibel’s pitch framework: the 30-second pitch in three sentences

    Michael provides a simple structure founders should be able to deliver anytime. Clarity beats jargon, and the goal is to start a real conversation quickly.

13. 13

    The 2-minute pitch: unique insight, business model, team, and the ask

    Michael extends the pitch to a compact two minutes by adding four components. The focus is on delivering an ‘aha,’ being crisp about monetization, and making a clear fundraising ask.

14. 14

    Fundraising timing & meeting setup + investor roleplay: bad pitch vs good pitch

    Michael explains why fundraising is easiest when you have leverage and how to run meetings in parallel. Dalton and Qasar then demonstrate a poor investor pitch and an improved version, highlighting what changes investor perception.