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Sep 16, 2018 · 25m · top-founders

1149 My investors kicked me out of my company, now personality tool at $1m+ ARR

Drew D'Agostino · 12m spoken Nathan Latka · 9m spoken
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

In this episode of the Top Entrepreneurs Podcast, host Nathan Latka interviews Crystal founder Drew D'Agostino about overcoming an early venture ouster to build an AI-driven personality prediction SaaS platform approaching $100k in monthly recurring revenue.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 44.8% of the talking time here. How this is scored →

Nathan as informed peer 4.8 Guest teaching 2.2 Guest disagreement 1.2 Nathan pushing back 3.6
05100:0010:0020:001:32–4:32 · Nathan as informed peer 4/10 Introducing Crystal and Personality Prediction Technology Latka tries to categorize Crystal as a sexier StrengthsFinder, prompting D'Agostino to clarify that Crystal predicts DISC personality profiles via NLP and public data rather than administering standard static questionnaires.4:32–10:27 · Nathan as informed peer 5/10 Freemium Growth Model and Dual Revenue Streams Latka pushes past D'Agostino's initial freemium answer to uncover paid SaaS and API tiers, then aggressively interrogates D'Agostino about his previous startup where venture investors ousted him at $1M ARR.10:28–12:55 · Nathan as informed peer 4/10 Bootstrapping Crystal to Raising Series A with Salesforce Latka questions D'Agostino on why he raised venture capital again after being burned previously, while D'Agostino explains setting strict deal breakers and partnering with Salesforce.12:59–18:22 · Nathan as informed peer 5/10 Sponsor Break: Relentless MV Event Following the sponsor break, Latka calculates MRR and growth velocity while D'Agostino walks through how changing profile limits reduced monthly net MRR churn from 7% down to under 3.5%.18:22–23:21 · Nathan as informed peer 6/10 Customer Acquisition, Series B Valuation, and Long-Term Vision Latka challenges D'Agostino on the risks of accepting a high 10x-plus revenue multiple that raises the minimum exit threshold, but D'Agostino defends building for a large long-term vision.1:32–4:32 · Guest teaching 4/10 Introducing Crystal and Personality Prediction Technology Latka tries to categorize Crystal as a sexier StrengthsFinder, prompting D'Agostino to clarify that Crystal predicts DISC personality profiles via NLP and public data rather than administering standard static questionnaires.4:32–10:27 · Guest teaching 2/10 Freemium Growth Model and Dual Revenue Streams Latka pushes past D'Agostino's initial freemium answer to uncover paid SaaS and API tiers, then aggressively interrogates D'Agostino about his previous startup where venture investors ousted him at $1M ARR.10:28–12:55 · Guest teaching 1/10 Bootstrapping Crystal to Raising Series A with Salesforce Latka questions D'Agostino on why he raised venture capital again after being burned previously, while D'Agostino explains setting strict deal breakers and partnering with Salesforce.12:59–18:22 · Guest teaching 2/10 Sponsor Break: Relentless MV Event Following the sponsor break, Latka calculates MRR and growth velocity while D'Agostino walks through how changing profile limits reduced monthly net MRR churn from 7% down to under 3.5%.18:22–23:21 · Guest teaching 2/10 Customer Acquisition, Series B Valuation, and Long-Term Vision Latka challenges D'Agostino on the risks of accepting a high 10x-plus revenue multiple that raises the minimum exit threshold, but D'Agostino defends building for a large long-term vision.1:32–4:32 · Guest disagreement 1/10 Introducing Crystal and Personality Prediction Technology Latka tries to categorize Crystal as a sexier StrengthsFinder, prompting D'Agostino to clarify that Crystal predicts DISC personality profiles via NLP and public data rather than administering standard static questionnaires.4:32–10:27 · Guest disagreement 1/10 Freemium Growth Model and Dual Revenue Streams Latka pushes past D'Agostino's initial freemium answer to uncover paid SaaS and API tiers, then aggressively interrogates D'Agostino about his previous startup where venture investors ousted him at $1M ARR.10:28–12:55 · Guest disagreement 1/10 Bootstrapping Crystal to Raising Series A with Salesforce Latka questions D'Agostino on why he raised venture capital again after being burned previously, while D'Agostino explains setting strict deal breakers and partnering with Salesforce.12:59–18:22 · Guest disagreement 1/10 Sponsor Break: Relentless MV Event Following the sponsor break, Latka calculates MRR and growth velocity while D'Agostino walks through how changing profile limits reduced monthly net MRR churn from 7% down to under 3.5%.18:22–23:21 · Guest disagreement 2/10 Customer Acquisition, Series B Valuation, and Long-Term Vision Latka challenges D'Agostino on the risks of accepting a high 10x-plus revenue multiple that raises the minimum exit threshold, but D'Agostino defends building for a large long-term vision.1:32–4:32 · Nathan pushing back 3/10 Introducing Crystal and Personality Prediction Technology Latka tries to categorize Crystal as a sexier StrengthsFinder, prompting D'Agostino to clarify that Crystal predicts DISC personality profiles via NLP and public data rather than administering standard static questionnaires.4:32–10:27 · Nathan pushing back 4/10 Freemium Growth Model and Dual Revenue Streams Latka pushes past D'Agostino's initial freemium answer to uncover paid SaaS and API tiers, then aggressively interrogates D'Agostino about his previous startup where venture investors ousted him at $1M ARR.10:28–12:55 · Nathan pushing back 3/10 Bootstrapping Crystal to Raising Series A with Salesforce Latka questions D'Agostino on why he raised venture capital again after being burned previously, while D'Agostino explains setting strict deal breakers and partnering with Salesforce.12:59–18:22 · Nathan pushing back 3/10 Sponsor Break: Relentless MV Event Following the sponsor break, Latka calculates MRR and growth velocity while D'Agostino walks through how changing profile limits reduced monthly net MRR churn from 7% down to under 3.5%.18:22–23:21 · Nathan pushing back 5/10 Customer Acquisition, Series B Valuation, and Long-Term Vision Latka challenges D'Agostino on the risks of accepting a high 10x-plus revenue multiple that raises the minimum exit threshold, but D'Agostino defends building for a large long-term vision.

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

0:00 · Nathan 66.3% · guest 33.7%0:00 · Nathan 66.3% · guest 33.7%3:00 · Nathan 42% · guest 58%3:00 · Nathan 42% · guest 58%6:00 · Nathan 33.5% · guest 66.5%6:00 · Nathan 33.5% · guest 66.5%9:00 · Nathan 30.2% · guest 69.8%9:00 · Nathan 30.2% · guest 69.8%12:00 · Nathan 63.2% · guest 36.8%12:00 · Nathan 63.2% · guest 36.8%15:00 · Nathan 25.3% · guest 74.7%15:00 · Nathan 25.3% · guest 74.7%18:00 · Nathan 49.1% · guest 50.9%18:00 · Nathan 49.1% · guest 50.9%21:00 · Nathan 36.5% · guest 63.5%21:00 · Nathan 36.5% · guest 63.5%24:00 · Nathan 68.5% · guest 31.5%24:00 · Nathan 68.5% · guest 31.5%
Sharpest disagreement ▶ 22:48 D'Agostino rejects taking quick exit money over long-term mission

D'Agostino rejects Latka's premise of flipping the business early for a quick payout, stating he turned down acquisition offers because he is dedicated to the multi-year vision.

 Hardest push from Nathan ▶ 21:47 Latka challenges the sustainability of raising at steep multiples

Latka presses D'Agostino on whether he worries about growing into a valuation north of a 10x multiple when standard industry acquisitions trade at 3-5x revenue.

 Biggest teaching moment ▶ 2:34 D'Agostino differentiates predictive personality AI from StrengthsFinder

D'Agostino educates Latka on the fundamental difference between standard survey questionnaires and machine learning models predicting DISC profiles from public text.

 Nathan holds their own ▶ 22:09 Latka breaks down M&A dynamics and venture return math

Latka demonstrates deep financial acumen by modeling how high valuations limit acquisition liquidity options for young founders.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Introducing Crystal and Personality Prediction Technology 4413 Latka tries to categorize Crystal as a sexier StrengthsFinder, prompting D'Agostino to clarify that Crystal predicts DISC personality profiles via NLP and public data rather than administering standard static questionnaires.
Freemium Growth Model and Dual Revenue Streams 5214 Latka pushes past D'Agostino's initial freemium answer to uncover paid SaaS and API tiers, then aggressively interrogates D'Agostino about his previous startup where venture investors ousted him at $1M ARR.
Bootstrapping Crystal to Raising Series A with Salesforce 4113 Latka questions D'Agostino on why he raised venture capital again after being burned previously, while D'Agostino explains setting strict deal breakers and partnering with Salesforce.
Sponsor Break: Relentless MV Event 5213 Following the sponsor break, Latka calculates MRR and growth velocity while D'Agostino walks through how changing profile limits reduced monthly net MRR churn from 7% down to under 3.5%.
Customer Acquisition, Series B Valuation, and Long-Term Vision 6225 Latka challenges D'Agostino on the risks of accepting a high 10x-plus revenue multiple that raises the minimum exit threshold, but D'Agostino defends building for a large long-term vision.

Statements from this episode (13)

Assertion Not checkable as stated
D'Agostino: Crystal has personality data on a few hundred million people
“So we offer access to a large set of personality data. For a few hundred million people”
Drew D'Agostino Sep 16, 2018 ▶ 2:06
Assertion Not checkable as stated
D'Agostino: Crystal predicts DISC personality type with 83% accuracy
“And 83% of the time we can properly guess what the primary personality type is when they take that assessment. So Crystal will get that about four to five times accurately.”
Drew D'Agostino Sep 16, 2018 ▶ 4:22
Assertion Not checkable as stated
D'Agostino: 70% of Crystal's revenue comes from $29/month SaaS accounts
“There's two main revenue streams. One is a pretty standard SaaS model, and that's a 29 dollar a month account to get unlimited access to our tools. So somebody who wants to install our Chrome extension can get access to Crystal profiles whenever they're lookin…”
Drew D'Agostino Sep 16, 2018 ▶ 5:35
Disclosure
D'Agostino and his co-founder were fired by Attend's investors
“That was a whole big thing where my co-founder and I got fired by our investors.”
Drew D'Agostino Sep 16, 2018 ▶ 6:33
Assertion Not checkable as stated
D'Agostino: Attend was nearing $1M ARR when investors fired founders
“I think we were about to hit a million ARR.”
Drew D'Agostino Sep 16, 2018 ▶ 9:02
Disclosure
D'Agostino rejected an Attend severance package to speak freely
“We actually got, we were offered a severance package in exchange for a release. But because if we signed that, I wouldn't be able to have this conversation with you at that level of specificity. So I prefer being able to speak and not filter myself.”
Drew D'Agostino Sep 16, 2018 ▶ 9:59
Disclosure
D'Agostino: Crystal has raised $7M in total capital to date
“We have raised a total of seven million.”
Drew D'Agostino Sep 16, 2018 ▶ 11:52
Disclosure
D'Agostino: Salesforce led Crystal's Series A and has been fantastic
“Salesforce, Salesforce is our lead investor, and obviously they're a huge, scary company, but they've been, like, fantastic”
Drew D'Agostino Sep 16, 2018 ▶ 12:31
Assertion Not checkable as stated
D'Agostino: Crystal approaches 2,000 customers in 2018
“We have about just coming up on 2000 customers now.”
Drew D'Agostino Sep 16, 2018 ▶ 14:29
Prediction Not checkable as stated
D'Agostino predicts Crystal will reach $100k MRR by December 2018
“Within, within three months.”
Drew D'Agostino Sep 16, 2018 ▶ 15:26
Disclosure
D'Agostino admits Crystal's monthly net MRR churn peaked around 7%
“The highest churn got to was consistently seeing seven, seven-ish percent net MRR churn per month.”
Drew D'Agostino Sep 16, 2018 ▶ 15:40
Prediction Not checkable as stated
D'Agostino: Crystal can reach 10% MoM revenue growth by year-end 2018
“So, so this year our projection my target is to average 10% month over month revenue growth. We're not there yet, and the reason that we, the reason that it's going to take a little while is because we've got a lot of that hangover churn but I'm pretty confide…”
Drew D'Agostino Sep 16, 2018 ▶ 17:54
Assertion Not checkable as stated
Crystal founder says self-service account LTV is just under $600
“On self-service accounts, LTV is just under 600.”
Drew D'Agostino Sep 16, 2018 ▶ 19:09
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