Startup founder Adam Joseph has never appeared on ‘Shark Tank,’ but he knows what it’s like to be in the hot seat in front of Marc Cuban.
Joseph was able to attract Cuban’s attention and investment in his AI-powered PR software tool, Clipbook, through a series of emails.
The seven-figure investment Joseph secured began 12 months ago with cold sensitization to some famous investors, including Cuban, who said he spends his days read and respond to emails.
Joseph shared highlights of his email exchange with Cuban exclusively with Business Insider. These emails show how Cuban responds to startup founders, evaluates business pitches and decides to invest via email, as the billionaire has said repeatedly.
“I wanted to offer a potential exit opportunity that I think could be a strong mutual fit,” Joseph wrote in his initial message to Cuban.
The Clipbook founder then provided a summary of his startup, which uses AI to track how people and businesses are discussed online, like a more sophisticated version of Google Alerts. Joseph worked in public relations for a few years and said he felt the “problems” of keeping tabs on public opinion, which he thought AI could help solve. When ChatGPT was launched By the end of 2022, Joseph said it was becoming “immediately obvious” that AI could transform public relations.
Cuban did not immediately respond to Joseph’s speech. The day after, the entrepreneur went on to add that he was endorsed by Dan Pfeiffer, co-host of the popular political show “Pod Save America.”
The same day, Cuban responded. He requested a sample report under his own name to demonstrate the technology in action. He also asked how Clipbook differed from Google Alerts and wanted to know what the founder expected of it – and under what conditions. From there, Joseph and Cuban exchanged a few more emails and made a call. Soon after, they reached an agreement, Joseph said.
“It happened more aggressively and faster with Mark than I expected,” Joseph later said in an interview with Business Insider.
Joseph said Cuban looked at it, not just the company.
“He was really doing a 360, just to test the pressure of the business,” Joseph said. “But I think probably the most important thing is to challenge myself as an entrepreneur. So the fact that he came 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 the email exchanges between Joseph and Cuban, which Joseph shared with Business Insider. Cuban gave Business Insider permission to publish his content. The original text and formatting have been retained, with slight edits for clarity. Some sensitive information, like email addresses and Clipbook revenue, has been redacted.
Adam Joseph to Mark Cuban — 12/28/2024 Subject: Opportunity to start Clipbook Hello Mr. Cuban, My name is Adam Joseph and I’m the CEO of Clipbook. I wanted to propose a potential Seed+ opportunity that I thought could be a strong mutual fit. I have copied the relevant details below:
About Us:
- Launched in January 2023.
- We are an AI-native research and analytics platform for communications, public relations, and government affairs teams. We automate the literature search essential for this large, traditional industry of knowledge workers.
Business & market thesis:
- Public relations and communications is a fast-paced and highly “manual” industry, comprised primarily of knowledge workers performing tasks manually, historically served by a thin legacy SaaS layer. (redacted)
- As a native AI solution, we will capture significant manual labor spend and introduce predictive capabilities through agentic AI.
- Consider Harvey AI, Hebbia AI or AlphaSense “for public relations and communications”
- Market size: Public relations, communications and government affairs represent a $100 billion expense for most knowledge workers.
Founder and CEO: Adam Joseph (Linkedin here)
- Former communications operator, BCG, Harvard, Fulbright. Based on SF.
Commercial traction:
- Income: (redacted)M YTD (2024) (cash basis) in <2 years. On (redacted) Profitable growth over one year.
- Burn: Positive cash flow (!)
Retention: (redacted) - Some customers: (redacted)
Funding:
- Bootstrapped until last month using customer revenue.
- In November, Commonweal Ventures seed investment closes – Ron Bloom (vice president of Brookfield Asset Management, 900 billion assets under management) of Commonweal Ventures. It was a competitive round and I received TS from other people, e.g. (redacted)
- Other investors include exited founders, including unicorn founder Jamie Beaton (WSJ profile hereCEO of Crimson Education, (redacted) top line).
Are you interested in investing? Happy to send you more/answer your questions. Best, Adam Joseph to Cuban — 12/29/2024 Hello Mr. Cuban, I realized I sent this email quite late in the evening, so I thought I’d leave a quick follow-up and add that Dan Pfeiffer – former White House communications director and chief strategist under President Obama (and top 10 chart podcaster Pod Save America) is also an investor. Cuban to Joseph — 12/29/2024 Can you send me a sample in my name (redacted) There are many content aggregators that deliver via email, including Google Alerts. Why couldn’t they do the same? What are you looking at (sic) for me and what do I get in return? Joseph to Cuban — 12/29/2024 Thank you very much for your response! Coming soon with an example for you. Would you like to chat live? I am at (redacted). Call anytime and I will answer. To answer your questions:
Content sources:
- We have signed agreements with (redacted) & (redacted)
- We don’t have any exclusives yet but overall we don’t think it’s a must to get us to 100M in ARR. (annual recurring income).
- Happy to discuss it, but I will mention that the greatest historical actor, (redacted)no longer has exclusivity with a major media provider as of this year. (They had Dow Jones/WSJ.)
Google Alerts: Simply put, Google Alerts is a consumer-facing tool that doesn’t meet the needs of a large business. This is why this segment
- Google Alerts can be useful for tracking, for example, a simple name or organization. But the $100 billion spent by knowledge workers on this has more nuanced needs for complex businesses.
For example (real life example from our client): Let’s say you are the Center for Audit Quality – the lobbying/advocacy group for the big audit firms (Big 4, e.g. Deloitte, PWC, etc.). You actively follow really important topics:
- The 4 big news concerning them (sic) major strategic initiatives around the audit profession
- Highlights (sic) industry groups and stakeholders – but only if the (sic) news
- Financial and policy-related policy announcements broken down by local, state and federal level
Other differentiators from existing Google alerts/tools:
- Eliminate humans from the workflow: savings of 100 hours for our users
- 1000x more precise, Comprehensive, predictive and personalized search capabilities using native AI technology. We can also search hundreds of topics, terms, stakeholders in parallel
- We access other data partnerships to integrate publisher impression data
- We integrate data sources not accessible to Google Alerts (e.g. add multi-modal search to TV, radio, podcasts, direct government data, competing websites, social media, etc. – other sources searched manually by these knowledge workers)
- Robust analytics and a host of other features that add value to customers
- The bottom line here on Google Alerts: they don’t move quickly and don’t dedicate time, resources, or innovation to the offering. This is not a strategic objective and we will act faster and more effectively than them.
On what I expect from you:
- (redacted)
(redacted)
- Open to a wide range of check sizes here depending on your appetite and open to discussion.
- So far we have raised funds entirely through YC SAFEs and Opportunity.
You represent a very strong strategic asset for us, given:
- Related to your past work in media/TMT/similar
- You value capital efficiency (as we clearly do after initially starting at over 1 million ARR) which is consistent with how we have rapidly scaled.
- We are AI / B2B SaaS
Thank you so much ! Best, Adam Cuban to Joseph — 12/31/2024 I’m traveling for the next few days. Go ahead and send the note. Are there any investor protections or is this the SAFE standard? Cuban to Joseph — 1/3/2025 Happy to answer any questions you may have. Let’s do it! M Joseph to Cuban — 1/3/2025 It looks good Probably some execution lessons I can learn from this I appreciate you – happy Friday Cuban to Joseph — 1/3/2025 lol. That’s the goal. Too many calls and meetings. Only fly if you’re making money or closing a deal. Otherwise zoom in. If you fail to convey the zoom, your message is not clear and focused. M