Tough Day AI Initial Email

Dear Friends of Red Bear Ventures:

RBV has secured a $200K allocation in the pre-seed financing of a very exciting company, Tough Day AI, that spun out of Cornell Tech last year and which was co-founded by Katherine von Jan (“KVJ”) and Alberto Escarlate.

KVJ was most recently the Chief Strategy Officer at Salesforce and Alberto is a serial CTO and the co-head of Startup Studio at Cornell Tech.

The company describes itself as follows: Tough Day AI superpowers workers to self-manage and succeed in a manager-lite workplace. It is the digital replica of a company's ideal manager - always available on demand to provide every employee with confidential, contextual, expert guidance that works.

The company’s investor pitch is here and we have scheduled a Zoom webinar with KVJ and Alberto for next Wednesday, February 12th at 1pm ET, which you can join here.

We are incredibly enthusiastic about Tough Day AI for multiple reasons:

• Tier 1 founders and team

• Remarkable customer traction in a very short period of time, including pilots with Google and Teneo, a paid pilot with Hawaii Employers Council (which works with 700+ companies), and a significant strategic partnership with Fisher Phillips - a top global labor and employment law firm

• A qualified revenue pipeline of $33M which includes Microsoft, ServiceNow, Gensler, Accuity, the State of Hawaii, and many others

• A large and untapped market opportunity driven by two important macro trends in the labor market:  “Unbossing” and “The Great Flattening” (detailed in the deck)

• Currently, no direct competition

• A technology moat which includes Constitutional AI, Hallucination Defense and Accountability Agents

• An AI data training moat based on partnerships with Fisher Philips (see above), Harvard Business Review, Forbes, Charterworks.com (Future of Work research and reporting by former WSJ, NYT, Wired writers), Equipt (for early career coaching), and Band of Sisters (authors and advisors on bias and unwritten rules of business)

• A go-to-market strategy based on large distribution partners which is already proving out, and which should allow Tough Day AI to capture a leading share of the market. This first-mover advantage is critical as it should give the company access to the most ongoing AI training data, which should in turn further improve Tough Day AI’s model, thereby creating sustainable, long-term differentiation for the platform.

• A “sweetheart” deal that RBV only has access to because of the Cornell ties to the company: this is a small $500K SAFE at a $10M cap. The company is doing this small round because it provides them with the additional capital to do a larger seed round this summer at a materially higher valuation once they have signed some significant customers in the pipeline (see above).  

Please join us for the webinar next Wednesday, after which we will distribute the Tough Day AI investment link via AngelList.  The syndicate will close on Wednesday, February 26th at 5pm ET.

Thanks!

Dan and Gus

Red Bear Ventures (RBV) is a community-first investment platform which invests exclusively in companies founded by, or managed by, the students, faculty, staff, and alumni of Cornell University, one of the world’s most innovative and entrepreneurial universities. RBV invests across stages and verticals and syndicates investment opportunities to the RBV community via special purpose vehicles (SPVs). RBV is an independent platform wholly managed by its Managing Partners - it is neither affiliated with, nor endorsed by, Cornell University.

More information can be found at www.redbear.vc.

Red Bear Ventures is a service mark used under license from its owner, Red Bear Angels Management LLC, which operates the angel group, Red Bear Angels. Please see www.RBAngels.com for information.