Startup founder Adam Joseph has never appeared on “Shark Tank,” but he knows how it feels to be on the hot seat in front of Mark Cuban.
Joseph managed to get Cuban’s attention and an investment in his AI-powered PR agency, Clipbook, through a series of emails.
The seven-figure investment that Joseph secured started 12 months ago with cold outreach to a few famous investors, including Cuban, who has said he spends his days reading and responding to emails.
Joseph shared highlights from his email exchange with Cuban exclusively with Business Insider. These emails show how Cuban responds to startup founders, assesses business pitches, and decides to invest over email, as the billionaire has said he’s done many times.
“I wanted to put a potential seed opportunity that I think might be a strong mutual fit,” Joseph wrote in his initial message to Cuban.
The Clipbook founder then provided a bullet-point summary of his startup, which uses AI to track how people and companies are being discussed online, like a more sophisticated version of Google Alerts. Joseph worked in PR for a few years and said he felt the “pain points” of keeping tabs on public sentiment, which he thought AI could help solve. When ChatGPT launched in late 2022, Joseph said it became “immediately obvious” that AI could transform PR.
Cuban didn’t respond to Joseph’s pitch right away. The next day, the entrepreneur followed up, adding that he’s backed by Dan Pfeiffer, co-host of the popular politics show “Pod Save America.”
That same day, Cuban responded. He requested a sample report for his own name to demonstrate the tech in action. He also asked how Clipbook differed from Google Alerts and wanted to know what the founder was seeking from him — and under what terms. From there, Joseph and Cuban traded a few more emails and hopped on a call. Soon after, they reached a deal, Joseph said.
“It moved more aggressively and faster with Mark than I expected,” Joseph later said in an interview with Business Insider.
Joseph said Cuban vetted him, not just the business.
“He was just really doing a 360, just pressure-testing the business,” Joseph said. “But I think more importantly, probably, pressure-testing me as an entrepreneur. So the fact that he had come in pretty hot with some pretty aggressive questions I think was also really — it was really, actually, in retrospect, a really positive signal that he was very interested in the deal.”
Below are email exchanges between Joseph and Cuban, which Joseph shared with Business Insider. Cuban gave Business Insider permission to publish their content. The original text and formatting have been preserved, with small modifications for clarity. Certain sensitive information, like email addresses and Clipbook’s revenue, has been redacted.
Adam Joseph to Mark Cuban — 12/28/2024 Subject: Clipbook seed opportunity Hello Mr. Cuban, My name is Adam Joseph and I’m the CEO of Clipbook. I wanted to put a potential seed+ opportunity that I think might be a strong mutual fit. I’ve copied below the pertinent details:
About us:
- Launched Jan 2023.
- We’re an AI-native research and analysis platform for communications, PR, and government affairs teams. We automate the essential desk research for this large, legacy industry of knowledge workers.
Company & market thesis:
- PR and communications is a rapidly changing & highly ‘manual’ legacy industry of mostly knowledge workers manually executing tasks- historically serviced by a thin legacy SaaS layer [redacted]
- As an AI-native solution, we will capture significant spend of manual knowledge work and introduce predictive capabilities through agentic AI.
- Think Harvey AI, Hebbia AI, or AlphaSense “for PR & Communications”
- Market size: PR, Comms, and Gov Affairs is a 100B spend of mostly knowledge workers.
Founder & CEO: Adam Joseph (Linkedin here)
- Former comms operator, BCG, Harvard, Fulbright. SF-based.
Commercial traction:
- Revenue: [redacted]M YTD (2024) (cash basis) in <2 years. Over [redacted] YoY profitable growth.
- Burn: Cash flow positive (!)
Retention: [redacted] - Some Customers: [redacted]
Funding:
- Bootstrapped until last month using revenue from customers.
- In November closed seed investment from Commonweal Ventures – Ron Bloom (Vice Chair at Brookfield Asset Management, 900B AUM) from Commonweal Ventures. It was a competitive round & I received TS’s from others, e.g. [redacted]
- Other investors include exited founders including unicorn founder Jamie Beaton (WSJ profile here, CEO Crimson Education, [redacted] topline).
Are you interested in investing? Happy to send along more / answer any questions. Best, Adam Joseph to Cuban — 12/29/2024 Hello Mr Cuban – realized I sent this email quite late in the evening, so thought I’d drop a quick follow-up and add that Dan Pfeiffer – former White House Communications Director & chief strategist under President Obama (and top 10 charts podcaster of Pod Save America) is also an investor. Cuban to Joseph — 12/29/2024 Can you send me a sample on my name [redacted] There are a lot of content aggregators that distribute via email, including Google alerts. Why couldn’t they do the same ? What are youooking [sic] for from me and what do I get for it ? Joseph to Cuban — 12/29/2024 Thanks so much for your response! Circling soon with an example for you. Would you like to chat live? I’m at [redacted]. Call anytime and I’ll answer. To answer your questions:
Content sources:
- We have signed agreements with [redacted] & [redacted]
- We don’t have exclusives yet but overall don’t think it is a must-have to get us to 100M in ARR [annual recurring revenue].
- Happy to discuss but will mention that the largest legacy player, [redacted], no longer has exclusivity with any major media provider as of this year. (They used to have Dow Jones / WSJ.)
Google Alerts: Simply put – Google Alerts is a consumer-level tool that does not meet the enterprise needs of a large business. It’s why this segment
- Google Alerts might be fine to track, say, track a simple name or org. But the 100B of spending of knowledge workers doing this has more nuanced needs for complex enterprises.
For example (real example from our client): say you are the Center for Audit Quality – the lobby / advocacy group for the large audit firms (Big 4, e.g. Deloitte, PWC, etc). You are actively tracking really important topics:
- Big 4 news as they pertains [sic] to big strategic initiatives around the audit business
- Salients [sic] industry groups & stakeholders – but only if the [sic] news
- Policy announcements related to finance & policy broken down by the local, state, and federal level
Other differentiators from Google Alerts / legacy tools:
- Take the human out of the loop for the workflow – savings 100s of hours for our users
- 1000x more precise, comprehensive, predictive, and tailored search capabilities using AI-native technology. We can also search hundreds of topics, terms, stakeholders in parallel
- We access other data partnerships to integrate impressions data from the publishers
- We integrate data sources not accessible to Google Alerts (e.g. add multi-modal search to TV, radio, podcast, direct government data, competitor websites, social media, etc – other sources manually searched by these knowledge workers)
- Robust analytics & flurry of other features set that add value to customers
- The bottom line here on Google Alerts: they aren’t moving quickly & putting the time, resources, or innovation on the offering. It’s not a strategic focus and we will move faster & more effectively than they will.
On what I’d like from you:
- [redacted]
[redacted]
- Open to broad check size range here depending on your appetite & open to discussing.
- We’ve raised entirely on YC SAFEs so far & expediency
You are a very strong strategic fit for us, given:
- Throughline with your past work in media / TMT / similar
- You value capital efficiency (as we clearly do having bootstrapped to over 1M in ARR initially) aligns with how we quickly scaled.
- We are AI / B2B SaaS
Thanks much! Best, Adam Cuban to Joseph — 12/31/2024 I’m travelling for the next few days. Go ahead and send the note. Are there any investor protections or is it standard SAFE? Cuban to Joseph — 1/3/2025 Happy to answer any questions you have. Let’s Get it done ! M Joseph to Cuban — 1/3/2025 Sounds good Probably some execution lessons I can learn from that Appreciate you – happy friday Cuban to Joseph — 1/3/2025 lol. Thats the goal. Too many calls and meetings. Only fly if you are getting money or closing a deal. Otherwise zoom. If you can’t convey in the zoom, your message isn’t crisp and on target M
