This Week in Startups: AI for Investors, Publisher Rewards, Sleep Tech & More – 2024 Jam with JCal Recap

Host: Jason Calacanis
Date: October 24, 2024
Episode: E2032

Episode Overview

In this special edition, Jason Calacanis recaps the standout sessions from "Jam with JCal," a segment spotlighting early-stage founders sharing their startups for live brainstorming and candid feedback. The episode focuses on five diverse, tech-enabled startups, each with their own unique domain—AI for financial advisors, dog yard sharing, architectural code compliance, sleep improvement, and publisher engagement rewards. Jason provides unfiltered advice on fundraising, design, product-market fit, pricing strategies, and go-to-market tactics, making the episode a masterclass in startup mentoring.

Featured Startups & Main Themes

1. Uptrends AI – AI-powered news for investment advisors
2. Roam App – Marketplace for yard sharing for dogs
3. Ulama – AI-powered code compliance for architects
4. CorePod – AI sleep and mental health companion device
5. Bonbon Tech – Publisher engagement & rewards platform

1. Uptrends AI: Automating News for Financial Advisors

Guest: Ramsey Schaefer, CEO/co-founder
Timestamps: [02:25] – [16:53]

Key Insights & Discussion

• Pain Point & Solution: Financial advisors are overwhelmed by information requests from clients about fast-changing stock events. Uptrends AI monitors thousands of data sources, summarizes actionable news, and delivers customized alerts and client-ready explanations.
• Business Model: Freemium, with $15/month (DIY) and $50/month (pro, aimed at advisors) subscriptions. Market size estimated at 300,000 U.S. advisors.
• Team: Small but technical, all founders/employees code; expertise in stock market and ML.

Jason’s Feedback & Quotes

• On Pitching:
  "Great job by the way. Overall the pitch is tight in that it explains to me what you do, who your customer is and what the product is." [05:18]

• On Pricing Strategy:
  "You are charging far too little... you should be charging 10% of the value you create, which is $10,000, which is $2,000 a year. You're charging $50/mo ($600/yr)... It's like they pay more for their Gmail account. Come on." [12:30]

• Design & Sales Advice:
  "Product looks okay. Needs a bit of a design refresh—too ‘techy’ not enough ‘finance’." [08:35] "Founder-led sales are critical in early days. You need to hear directly from customer zero, one, two, three..." [09:12]

• Go After High-Value Users:
  "Laser focus, not on the number of customers, but on landing the big whales... go after the really high-end here." [12:30]

• Collaboration & Customer Feedback:
  "Discord group, iMessage—keep involving users directly in product building!" [15:49]

• Memorable Moment:
  "You made yourself likable. You're thoughtful... I think lean into that a little bit, like a little bit of drive. Don’t be too mellow." [16:53]

2. Roam App: Yard Sharing for Dogs

Guest: Anna Malhotra, co-founder/CEO
Timestamps: [18:05] – [31:27]

Key Insights & Discussion

• Core Problem: Many dogs aren’t suited for public parks; urban dog owners struggle to find safe, off-leash play areas.
• Marketplace Challenge: Difficult to acquire "good supply" (quality yards) before activating demand.
• Tactics Tried: Network outreach, classifieds, Nextdoor, failed attempts at door-to-door and direct contact via rival apps like Rover.

Jason’s Feedback & Quotes

• Supply Acquisition Hack:
  "Go to existing Airbnb and VRBO owners. People love founders, they love startups. Say: 'Hey, we’re like Airbnb for dog runs, draft on Airbnb’s existing network!'" [21:10]

• Direct Approaches:
  "Go on Reddit subforums, float the idea, start gray-market conversations." [24:20]

• Macro-View – Build a Third Space:
  "What about renting a crummy house in Queen Anne, $4-5K a month, turn the backyard into 20 pens? Sell coffee, add dog grooming. Become the Starbucks of dog runs—a true third space for people and their dogs." [28:41]

• Expansion Advice:
  "Maybe the wedge is antisocial dogs, but dog training, concessions, grooming—think bigger about what else the community wants." [31:00]

• Memorable Moment:
  Anna, on the feedback, "Am I allowed to say 11?" Jason: "Now we're really jamming!" [31:19]

3. Ulama: AI for Code Compliance in Architecture

Guest: Tyce Herman, founder
Timestamps: [32:50] – [46:53]

Key Insights & Discussion

• Product: Plugin for architects (mainly Revit), auto-checks 3D building models for code compliance (ADA, building codes), reduces costly mistakes, and speeds up approval process.
• Technical Approach: AI/multimodal approach parses building codes, runs real-time checks within design process.

Jason’s Feedback & Quotes

• Ecosystem Strategy:
  "How Autodesk features you and your App Store relationships is the key driver… Builds a dependency, but also an acquisition path." [40:21] "Bear hug... embed yourself into a firm where architects are using it daily—get desks in the middle of the action." [41:30]

• Launch Tactics:
  "Find 10-50 highly-influential architects across YouTube, Reddit, Instagram… build a Product Advisory Council. 'Hot embers'—each is a coal, together they spread heat and influence." [43:27]

• On Niche Markets:
  "This isn’t Uber—success is ten thousand paying customers, not ten million." [45:57]

4. CorePod: AI Sleep & Mental Health ‘Companion’ Device

Guest: Ulan, founder
Timestamps: [47:15] – [57:22]

Key Insights & Discussion

• Concept: Physical AI-powered smart speaker (with a “dog” avatar) offering conversational mental support, relaxation, and sleep coaching. B2C hardware/software hybrid.
• Target Audience: High-stress, medium/high-income consumers interested in mental health.
• Go-to-Market Challenge: Hardware is "twice as hard" as B2C software; proving efficacy is tough.

Jason’s Feedback & Quotes

• Focus on Core Value Before Hardware:
  "Are you passionate about hardware, or do you want to help people sleep? Prove your interactive sleep coach actually works—do it as an app BEFORE building a device." [52:14]
  "Can a language model put someone to bed like mom or dad did reading a story?" [55:58]

• Advice on Market Proving:
  "Get 100 people from insomnia Reddit, Craigslist at 1am... pay them a $10 gift card to try it for three nights. See what you learn, iterate from there." [54:50]

• Concerns on Hardware:
  "Raising money for hardware + mental health in 2024 is the hardest thing—far better to show seed investors a small real-world test first." [57:22]

5. Bonbon Tech: Publisher Rewards & Engagement Platform

Guest: Elliot Easterling, CEO
Timestamps: [58:12] – [77:41]

Key Insights & Discussion

• Value Proposition: Rewards program for publishers to increase registration, gather first-party data, and fight declining traffic caused by cookie deprecation, algorithm changes, and AI-driven platform stickiness.
• Mechanics: Offers sweepstakes, points for engagement (read articles, watch videos), gamified registration to deepen profiles; syndicates expensive prizes across publisher network.
• Scale: 60,000+ registered users, 60 million monthly pageviews across 27 sites.

Jason’s Feedback & Quotes

• Publisher Market Caveats:
  "Publishers are struggling—their budgets are small. Sometimes it’s like selling deck chairs on the Titanic." [64:09] "I’d rather see this on growing formats—TikTok, podcasts, shorts—catch a bigger wave." [74:10]

• On Funding & Network Effects:
  "Network-based businesses do have a carve out. Show viral growth, run small but vivid experiments with sweepstakes to prove engagement, then add zeros." [69:18] "You really gotta get some market pull. Might need to find another beach where the waves are a little bigger." [76:59]

• Tactical Gamification:
  "Tried & true: refer a friend, invite a member for points... just like Robinhood, Uber, Dropbox." [67:49]

Notable Quotes by Jason Calacanis

• On Early-stage Experimentation:
  "Sometimes the wedge—like antisocial dogs—gets you there, but the wedge just opens the door to something bigger.” [31:00]

• On Building Founder-Investor Trust:
  “You gotta be able to go back-and-forth quickly. In just 15 minutes together, we had a great volley…like pickleball or ping pong." [16:53]

• On Startup Beach Selection:
  “A surfer is only as good as the waves presented to them… Sometimes, you might be surfing at a beach where the tide’s going out faster than you can build a business.” [74:10]

Timestamps for Key Segments

• Uptrends AI (AI for Investors): [02:25] – [16:53]
• Roam App (Yard Sharing for Dogs): [18:05] – [31:27]
• Ulama (AI for Architectural Compliance): [32:50] – [46:53]
• CorePod (AI Sleep Companion): [47:15] – [57:22]
• Bonbon Tech (Publisher Rewards Platform): [58:12] – [77:41]

Tone & Takeaways

The episode is frank, rapid-fire, supportive but never sugarcoated—classic JCal. Founders get immediate, actionable advice and are challenged to re-think their assumptions, sharpen their value props, and experiment relentlessly. Key through-lines include:

• Obsessive focus on true customer value and pricing accordingly
• Doing founder-led sales and research before scaling or raising
• Building thoughtful, slow “hot embers” communities of early, influential users
• Targeting growing, not shrinking, markets
• Running small, vivid experiments before big spend

For founders, investors, and product folks, this recap is a goldmine of current best-practices and tough-love startup advice from Jason Calacanis.