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Jan 27, 2017 · 26m · 20vc

20VC: Why You Should Build Your Investor Team Like A Sports Team & How To Leverage The Abilities Of Your Investors Effectively with Ted Blosser, Founder & CEO @ WorkRamp

Ted Blosser · 16m spoken Harry Stebbings · 8m spoken
0:00 / 0:00

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In this episode of The 20 Minute VC, host Harry Stebbings interviews Ted Blosser, Founder and CEO of WorkRamp, about building high-performing investor syndicates, key learnings from scaling Box, and tactical fundraising strategies for early-stage enterprise startups.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 35.1% of the talking time here. How this is scored →

Harry as informed peer 2.7 Guest teaching 4.3 Guest disagreement 1.3 Harry pushing back 1.8
05100:0010:0020:002:28–4:32 · Harry as informed peer 1/10 Ted Blosser's Background and Founding WorkRamp Harry opens with a warm introduction and asks for Ted's background. Ted details his failed first startup, his five-year tenure at Box learning under Aaron Levie, and how enterprise training gaps inspired WorkRamp.4:33–7:45 · Harry as informed peer 2/10 Key Takeaways from Box and Enterprise Brand Building Harry asks about key takeaways from Box's hyper-growth. Ted reframes the standard startup belief that the best product wins, explaining that in enterprise software, brand strength drives market dominance over pure product capabilities.7:47–10:42 · Harry as informed peer 2/10 Structuring an Investor Base Like a Sports Team Ted rejects the classic mentor advice of picking investors like spouses, presenting a contrarian sports team framework where each investor fulfills a distinct positional role. Harry prompts him to detail how specific angels and funds fit into this model.10:43–14:39 · Harry as informed peer 6/10 Fundraising Dynamics, Runway Planning, and Product-Market Fit When Ted offers a vague 18-to-24 month runway range, Harry forcefully pushes back, calling it a politician's answer and demanding specific commitment. Harry later demonstrates industry expertise by citing Justin Kan's metric of ten unaffiliated customers for product-market fit.14:43–18:42 · Harry as informed peer 3/10 Founder Gratitude, Aaron Levie Story, and Y Combinator Lessons Harry asks a reflective question about founder gratitude, prompting Ted to share stories about Aaron Levie's relentless focus post-quarterly wins and Y Combinator peer network dynamics. The exchange is highly collaborative and conversational.18:42–24:16 · Harry as informed peer 2/10 Short-Term vs. Long-Term Investor Value Add Ted critiques seed investors who claim to be long-term but overly fixate on early metrics like LTV and CAC during due diligence. Harry then transitions into a swift quickfire round covering books, diversity policies, Jeff Bezos, and future goals.2:28–4:32 · Guest teaching 3/10 Ted Blosser's Background and Founding WorkRamp Harry opens with a warm introduction and asks for Ted's background. Ted details his failed first startup, his five-year tenure at Box learning under Aaron Levie, and how enterprise training gaps inspired WorkRamp.4:33–7:45 · Guest teaching 5/10 Key Takeaways from Box and Enterprise Brand Building Harry asks about key takeaways from Box's hyper-growth. Ted reframes the standard startup belief that the best product wins, explaining that in enterprise software, brand strength drives market dominance over pure product capabilities.7:47–10:42 · Guest teaching 5/10 Structuring an Investor Base Like a Sports Team Ted rejects the classic mentor advice of picking investors like spouses, presenting a contrarian sports team framework where each investor fulfills a distinct positional role. Harry prompts him to detail how specific angels and funds fit into this model.10:43–14:39 · Guest teaching 5/10 Fundraising Dynamics, Runway Planning, and Product-Market Fit When Ted offers a vague 18-to-24 month runway range, Harry forcefully pushes back, calling it a politician's answer and demanding specific commitment. Harry later demonstrates industry expertise by citing Justin Kan's metric of ten unaffiliated customers for product-market fit.14:43–18:42 · Guest teaching 4/10 Founder Gratitude, Aaron Levie Story, and Y Combinator Lessons Harry asks a reflective question about founder gratitude, prompting Ted to share stories about Aaron Levie's relentless focus post-quarterly wins and Y Combinator peer network dynamics. The exchange is highly collaborative and conversational.18:42–24:16 · Guest teaching 4/10 Short-Term vs. Long-Term Investor Value Add Ted critiques seed investors who claim to be long-term but overly fixate on early metrics like LTV and CAC during due diligence. Harry then transitions into a swift quickfire round covering books, diversity policies, Jeff Bezos, and future goals.2:28–4:32 · Guest disagreement 0/10 Ted Blosser's Background and Founding WorkRamp Harry opens with a warm introduction and asks for Ted's background. Ted details his failed first startup, his five-year tenure at Box learning under Aaron Levie, and how enterprise training gaps inspired WorkRamp.4:33–7:45 · Guest disagreement 1/10 Key Takeaways from Box and Enterprise Brand Building Harry asks about key takeaways from Box's hyper-growth. Ted reframes the standard startup belief that the best product wins, explaining that in enterprise software, brand strength drives market dominance over pure product capabilities.7:47–10:42 · Guest disagreement 2/10 Structuring an Investor Base Like a Sports Team Ted rejects the classic mentor advice of picking investors like spouses, presenting a contrarian sports team framework where each investor fulfills a distinct positional role. Harry prompts him to detail how specific angels and funds fit into this model.10:43–14:39 · Guest disagreement 2/10 Fundraising Dynamics, Runway Planning, and Product-Market Fit When Ted offers a vague 18-to-24 month runway range, Harry forcefully pushes back, calling it a politician's answer and demanding specific commitment. Harry later demonstrates industry expertise by citing Justin Kan's metric of ten unaffiliated customers for product-market fit.14:43–18:42 · Guest disagreement 1/10 Founder Gratitude, Aaron Levie Story, and Y Combinator Lessons Harry asks a reflective question about founder gratitude, prompting Ted to share stories about Aaron Levie's relentless focus post-quarterly wins and Y Combinator peer network dynamics. The exchange is highly collaborative and conversational.18:42–24:16 · Guest disagreement 2/10 Short-Term vs. Long-Term Investor Value Add Ted critiques seed investors who claim to be long-term but overly fixate on early metrics like LTV and CAC during due diligence. Harry then transitions into a swift quickfire round covering books, diversity policies, Jeff Bezos, and future goals.2:28–4:32 · Harry pushing back 0/10 Ted Blosser's Background and Founding WorkRamp Harry opens with a warm introduction and asks for Ted's background. Ted details his failed first startup, his five-year tenure at Box learning under Aaron Levie, and how enterprise training gaps inspired WorkRamp.4:33–7:45 · Harry pushing back 1/10 Key Takeaways from Box and Enterprise Brand Building Harry asks about key takeaways from Box's hyper-growth. Ted reframes the standard startup belief that the best product wins, explaining that in enterprise software, brand strength drives market dominance over pure product capabilities.7:47–10:42 · Harry pushing back 1/10 Structuring an Investor Base Like a Sports Team Ted rejects the classic mentor advice of picking investors like spouses, presenting a contrarian sports team framework where each investor fulfills a distinct positional role. Harry prompts him to detail how specific angels and funds fit into this model.10:43–14:39 · Harry pushing back 7/10 Fundraising Dynamics, Runway Planning, and Product-Market Fit When Ted offers a vague 18-to-24 month runway range, Harry forcefully pushes back, calling it a politician's answer and demanding specific commitment. Harry later demonstrates industry expertise by citing Justin Kan's metric of ten unaffiliated customers for product-market fit.14:43–18:42 · Harry pushing back 1/10 Founder Gratitude, Aaron Levie Story, and Y Combinator Lessons Harry asks a reflective question about founder gratitude, prompting Ted to share stories about Aaron Levie's relentless focus post-quarterly wins and Y Combinator peer network dynamics. The exchange is highly collaborative and conversational.18:42–24:16 · Harry pushing back 1/10 Short-Term vs. Long-Term Investor Value Add Ted critiques seed investors who claim to be long-term but overly fixate on early metrics like LTV and CAC during due diligence. Harry then transitions into a swift quickfire round covering books, diversity policies, Jeff Bezos, and future goals.

speaking balance: gold is Harry, purple is the guest (3 minute bins)

0:00 · Harry 87.6% · guest 12.4%0:00 · Harry 87.6% · guest 12.4%3:00 · Harry 8.3% · guest 91.7%3:00 · Harry 8.3% · guest 91.7%6:00 · Harry 23.3% · guest 76.7%6:00 · Harry 23.3% · guest 76.7%9:00 · Harry 24.3% · guest 75.7%9:00 · Harry 24.3% · guest 75.7%12:00 · Harry 28.7% · guest 71.3%12:00 · Harry 28.7% · guest 71.3%15:00 · Harry 24.3% · guest 75.7%15:00 · Harry 24.3% · guest 75.7%18:00 · Harry 23.4% · guest 76.6%18:00 · Harry 23.4% · guest 76.6%21:00 · Harry 18.8% · guest 81.2%21:00 · Harry 18.8% · guest 81.2%24:00 · Harry 94.2% · guest 5.8%24:00 · Harry 94.2% · guest 5.8%
Sharpest disagreement ▶ 8:09 Rejecting the VC-as-spouse paradigm

Ted directly challenges conventional startup wisdom, rejecting the widely accepted advice that founders should pick investors like spouses in favor of a sports team metaphor.

 Hardest push from Harry ▶ 12:11 Calling out the politician's answer

Harry refuses to accept Ted's vague 18-to-24 month runway response, explicitly calling it a politician's answer and forcing him to clarify the exact numbers.

 Biggest teaching moment ▶ 6:37 Reframing enterprise product vs brand

Ted educates the host on enterprise sales dynamics, dispelling the common myth that product quality wins deals by pointing out that superior brand power drove success for giants like Salesforce and NetSuite.

 Harry holds his own ▶ 13:13 Citing Justin Kan's PMF benchmark

Harry displays notable industry knowledge and domain expertise by introducing Justin Kan's specific framework of ten unaffiliated customers to challenge definitions of product-market fit.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Ted Blosser's Background and Founding WorkRamp 1300 Harry opens with a warm introduction and asks for Ted's background. Ted details his failed first startup, his five-year tenure at Box learning under Aaron Levie, and how enterprise training gaps inspired WorkRamp.
Key Takeaways from Box and Enterprise Brand Building 2511 Harry asks about key takeaways from Box's hyper-growth. Ted reframes the standard startup belief that the best product wins, explaining that in enterprise software, brand strength drives market dominance over pure product capabilities.
Structuring an Investor Base Like a Sports Team 2521 Ted rejects the classic mentor advice of picking investors like spouses, presenting a contrarian sports team framework where each investor fulfills a distinct positional role. Harry prompts him to detail how specific angels and funds fit into this model.
Fundraising Dynamics, Runway Planning, and Product-Market Fit 6527 When Ted offers a vague 18-to-24 month runway range, Harry forcefully pushes back, calling it a politician's answer and demanding specific commitment. Harry later demonstrates industry expertise by citing Justin Kan's metric of ten unaffiliated customers for product-market fit.
Founder Gratitude, Aaron Levie Story, and Y Combinator Lessons 3411 Harry asks a reflective question about founder gratitude, prompting Ted to share stories about Aaron Levie's relentless focus post-quarterly wins and Y Combinator peer network dynamics. The exchange is highly collaborative and conversational.
Short-Term vs. Long-Term Investor Value Add 2421 Ted critiques seed investors who claim to be long-term but overly fixate on early metrics like LTV and CAC during due diligence. Harry then transitions into a swift quickfire round covering books, diversity policies, Jeff Bezos, and future goals.

Statements from this episode (8)

Assertion Supported
Blosser: First startup combining mobile, social, and local was a total failure
“In my mid-twenties, I actually founded my first startup, and it was a huge failure. Pretty much Took everything that was hot at the time, whether it be mobile, social, and local, and try to combine it all into one startup, and it failed pretty, pretty miserabl…”
Ted Blosser Jan 27, 2017 ▶ 2:45
Opinion
Blosser: Salesforce succeeds due to brand power rather than product quality
“If you look at Salesforce.com and they don't have the best product in the world, but they have the best brand.”
Ted Blosser Jan 27, 2017 ▶ 6:57
Disclosure
Blosser: Initialized hired Kim-Mai Cutler to coach portfolio enterprise branding
“I know Gary Tan and Alexis Ohanian from our investors at Initialize, they've been very, very good in helping us build our brand. They brought on Kim Mai Cutler onto their team from TechCrunch, and she's been extremely helpful in actually coaching us through ho…”
Ted Blosser Jan 27, 2017 ▶ 7:29
Insight
Ted Blosser: Founders should build investor teams like sports rosters, not marriages
“Don't just look at it as a spouse you would look for, but really look at it as a team you're building and think about the skill set that each VC brings to the table.”
Ted Blosser Jan 27, 2017 ▶ 8:30
Disclosure
WorkRamp chose Initialized to apply consumer growth tactics to enterprise software
“We went to them because not because they were hardcore enterprise seed investors, but really because they understood consumer markets extremely well. And we wanted to apply those same growth strategies to the enterprise market”
Ted Blosser Jan 27, 2017 ▶ 9:04
Disclosure
Blosser: WorkRamp capped seed round at $1.8M to enforce operational discipline
“And so and we actually did cap it. I think we actually, we raised about 1.8 million and we didn't want to raise much more past that. I mean, we had the opportunity to, but we ended up turning down money towards the end, really because we thought that was enoug…”
Ted Blosser Jan 27, 2017 ▶ 12:29
Assertion Not publicly verifiable
Blosser: YC partner Paul Buchheit told 100 batch startups none had PMF
“I remember when we were leaving YC, Paul Buchite sat the entire batch down, so all hundred companies or so, and he told us on our last day, he said, look, none of you guys are at product market fit, and we were looking around the room, and it was, we had some …”
Ted Blosser Jan 27, 2017 ▶ 13:20
Insight
Ted Blosser: Investors hyper-focused on early CAC and LTV lack long-term vision
“You can tell that even with small things like how they do due diligence, you see the ones that are focusing It's extremely on the, just the small metrics early on, like LTV or customer acquisition costs. They're not really looking at the long game.”
Ted Blosser Jan 27, 2017 ▶ 19:23
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