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JM

Jesse Middleton

7episodes
1podcast

Featured On 1 Podcast

All Appearances

7 episodes

AI Summary

→ WHAT IT COVERS Three pre-seed founders pitch three VCs live in New York City with only 15 minutes each — half the usual 45-minute format. Uche AI (consumer data for textured hair), Greener (trucking emissions tracking), and Wiggle Room (daycare management software) compete for real investment, resulting in the show's first-ever live funding commitments totaling $170,000 for Wiggle Room. → KEY INSIGHTS - **Compressed pitch format:** Founders can generate genuine investor conviction in 15 minutes rather than 45 when the pitch is tightly structured around traction, business model, and use of proceeds. All three founders finished under time, with two completing in 11 and 13 minutes respectively. Clarity of narrative and pre-validated metrics matter more than time spent in the room. - **B2B data monetization from consumer behavior:** Uche AI charges brands $10,000 per team annually (targeting $50,000 average ACV) for access to real-time consumer scan data collected via free barcode-scanning tools in stores. Starting in brand marketing and expanding to product development and category management allows a land-and-expand model targeting $1M ARR within 12 months from 25 logos. - **Inbound pipeline through organic content:** Uche AI built a $2.2M warm B2B pipeline almost entirely bootstrapped by creating evergreen educational content optimized for search. Brands discovered the platform through their own users, producing a seven-day sales cycle for the first Sephora deal. Founders should prioritize content that generates authority before pursuing outbound enterprise sales. - **Shipper-led adoption as a B2B channel strategy:** Greener pivoted from selling directly to trucking fleets toward having Fortune 500 shippers mandate the platform across their carrier networks. This approach compresses sales cycles — six enterprise proposals went out within 4.5 months versus an expected 9–12 month cycle — and turns large customers into distribution channels rather than just revenue sources. - **Pre-product sales to validate pricing and demand:** Wiggle Room made its first sale before building the product, charging $400 per daycare for an enrollment automation tool. The founder called 50 potential customers to test price sensitivity before setting it. This approach generated 50 paying customers with zero churn and 100% day-one activation, providing proof of demand before raising a $1M pre-seed round. - **Network-based distribution for deskless, low-tech SMBs:** Wiggle Room reaches childcare providers through national affiliate organizations, quality improvement specialists, and industry webinars rather than direct sales. Paid media targeting providers late at night — when administrative stress peaks — supplements network referrals. This two-channel approach (trusted networks plus targeted digital) reduces CAC for a fragmented, 200,000-unit market of solo operators. → NOTABLE MOMENT During live deliberations, Jenny Fielding initially offered a personal angel check to Wiggle Room due to a perceived fund conflict with a portfolio company. After the show, she reversed course and committed $50,000 from her fund instead — a reversal that, combined with Jesse Middleton and The Pitch Fund, brought Wiggle Room's total live-show raise to $170,000. 💼 SPONSORS [{"name": "Adobe Acrobat", "url": "https://adobe.com/dothatwithacrobat"}] 🏷️ Pre-Seed Fundraising, Startup Pitching, Consumer Data Platforms, Supply Chain Emissions, Childcare Tech, B2B SaaS

The Pitch

#179 Minimis: Declaring War on Garmin

The Pitch
42 minInvestor, Flybridge

AI Summary

→ WHAT IT COVERS Australian co-founders Joe and Paul pitch Minimus FLOW AR — fully standalone smart sunglasses for runners and cyclists displaying real-time stats via heads-up display — seeking $2M at a $699 retail price point. All four investors pass, citing prototype form factor concerns, but the founders later raise $270K and secure 11 bike shop distribution deals. → KEY INSIGHTS - **Prototype presentation strategy:** Bring a 3D-printed mockup of the target form factor alongside any functional prototype. All four investors passed primarily because they couldn't visualize the final Oakley-style design from the bulky Frankenstein prototype. A non-functional visual model bridges the imagination gap and keeps investors focused on the vision rather than current hardware limitations. - **Standalone vs. connected hardware:** Validate whether standalone functionality is truly a core user requirement before engineering it in, as it dramatically increases complexity and cost. Minimus found through customer research that users wanted phone-free running, but investors noted that most recreational athletes still carry phones for music and podcasts, suggesting the feature may only resonate with competitive triathletes and dedicated cyclists. - **Price point segmentation:** At $699 COGS of $350 dropping to $200 at volume, the product targets competitive triathletes and cyclists who spend $20,000 on bikes. Investors noted a $300 price point would open a broader addressable market. Hardware founders should map price sensitivity across athlete segments before committing to a production cost structure that locks in a premium-only customer base. - **Competitor validation as a sales tool:** When Meta released Strava-integrated Oakley glasses weeks after the pitch, Minimus used the press coverage as passive market education. Joe pitched 50 bike shops in San Francisco, converting roughly 11, by referencing the Meta announcement. Founders in emerging hardware categories can leverage big-tech adjacent launches to accelerate retail conversations without spending their own marketing budget. - **Accelerator geography matters:** Joining Founders Inc's Blueprint program in San Francisco — a hardware-focused cohort of 50 builders — enabled Minimus to iterate prototypes using professional lab equipment while simultaneously pitching local retailers and angel investors. The three-month Bay Area stay directly produced their first VC check from Entrepreneur Ventures plus 18 angel investors, demonstrating that physical proximity to hardware ecosystems compounds fundraising momentum. → NOTABLE MOMENT Six months after being rejected by all four investors, Joe cycled into San Francisco bike shops cold and converted roughly 11 out of 50 into signed distribution agreements — a conversion rate achieved largely by opening with his near-crash story, a pitch structure recommended by their coach Mark Danenberg. 💼 SPONSORS [{"name": "Adobe Acrobat Studio", "url": "https://adobe.com"}] 🏷️ Augmented Reality Hardware, Sports Wearables, Consumer Hardware Fundraising, Go-To-Market Strategy, Early-Stage Prototyping

The Pitch

#177 Aleoop: Show Me The Sales!

The Pitch
40 minInvestor, Flybridge

AI Summary

→ WHAT IT COVERS Megan Scanlon pitches Aleoop, a machine learning platform that extracts product insights from sales conversations to help B2B tech companies prioritize roadmaps. She seeks $1 million pre-seed funding while running five unpaid pilots, facing investor skepticism about converting free trials to her $15,000 annual contract value target. → KEY INSIGHTS - **Free-to-Paid Conversion Risk:** Running extended unpaid proof-of-concept periods creates dangerous precedent in B2B sales. Megan offers four-week free trials before transitioning to $15,000 annual contracts at $50 per user monthly with 25-user minimums, but investors challenge whether free customers will convert without demonstrated ROI metrics tied to specific revenue outcomes or time savings. - **Product-Sales Alignment Data:** Aleoop ingests unstructured feedback from Gong, Slack, Jira, Salesforce, and email through proprietary ML models to identify product gaps blocking deals. The platform dollarizes insights by connecting to CRM records, showing affected pipeline value and enabling product teams to prioritize roadmap decisions based on revenue at risk rather than subjective opinions or internal politics. - **Timing Product Launches:** Megan's ML models went live in July, giving only six weeks of functional technology before pitching in August. Investors identify this timing gap as critical—she needs ninety days of customer usage data to generate case studies showing quantified outcomes like unknown product gaps identified, dollars saved, or sales cycle acceleration before commanding premium pricing. - **Customer Qualification Discipline:** Megan disqualified three of five initial pilot customers, focusing on Series B-C companies with 100-plus employees, $10 million-plus revenue, and complex sales cycles. This rigorous ideal customer profile targeting—rather than accepting any interested prospect—proves essential for building repeatable sales processes and generating relevant case studies for future enterprise deals. - **Strategic Angel Leverage:** Meeting investors at pitch events yields immediate customer opportunities beyond capital. Yev from Backblaze provided a $10,000 angel investment plus warm introductions that converted Backblaze into a proof-of-concept customer within minutes of Megan's pitch, demonstrating how strategic angels deliver distribution advantages that accelerate early traction beyond their check size. → NOTABLE MOMENT Investor Mike Ma challenges Megan on why she built anything besides SOC 2 compliance if her own Aleoop analysis showed compliance blocking her entire pipeline. He pushes her to defend whether she truly believes her product roadmap decisions or if she's building features without market validation, forcing her to confront the gap between product vision and customer-driven development. 💼 SPONSORS [{"name": "Adobe Acrobat Studio", "url": "https://adobe.com/dothatwithacrobat"}] 🏷️ B2B SaaS Sales, Product-Market Fit, Pre-Seed Fundraising, Sales-Product Alignment, Pilot Conversion Strategy

AI Summary

→ WHAT IT COVERS Original Sunshine founders Brad and David pitch their gluten-free wheat-based bagel company to investors, revealing $1.6M in 2024 sales and securing multiple angel investments at a $9M post-money valuation. → KEY INSIGHTS - **Stealth product validation:** Founders served gluten-free bagels to VCs and guests for multiple days without revealing they were gluten-free, proving product quality matches traditional bagels before the pitch even began. - **Distribution strategy:** Securing Dot Foods distribution eliminates 15-20 weekly invoices, reduces shipping from LTL to truckload pickup, and enables single-case orders nationwide versus pallet minimums, dramatically improving margins from 37% to 44%. - **Revenue trajectory:** Company grew from $660K in 2023 to $1.6M in 2024, projecting $3.5M for 2025 and $10M by 2026 while maintaining profitability through food service focus over retail. - **Proprietary technology moat:** Three-layer defensibility includes custom ingredient sourcing, proprietary dry-blend flour formulation, and in-house conversion process to baked goods, making the gluten-free wheat starch formula difficult to reverse-engineer. → NOTABLE MOMENT When Black Seed Bagels called wanting their product, founder David flew from Mexico City to LA on New Year's Eve, picked up bagels, and hand-delivered them to New York to fulfill the order. 💼 SPONSORS [{"name": "Midi Health", "url": "joinmidi.com"}, {"name": "Strawberry.me", "url": "strawberry.me/unstuck"}, {"name": "CarMax", "url": "carmax.com"}] 🏷️ CPG Fundraising, Food Service Distribution, Gluten-Free Products, Angel Investing

The Pitch

#172 My Town AI: ChatGPT Meets SimCity

The Pitch
43 minInvestor from Flybridge

AI Summary

→ WHAT IT COVERS Nicole Sterling pitches My Town AI, an AI platform serving local governments under 50,000 residents. She seeks $1M pre-seed funding at $7M valuation, having raised $435K and onboarded eight pilot towns at $55-250 monthly pricing. → KEY INSIGHTS - **Discretionary budget strategy:** Small towns have purchasing authority up to $10,000 without RFP processes, enabling sole-source procurement. This creates faster sales cycles than large city contracts requiring competitive bidding and multiple stakeholder approvals across departments. - **Pricing architecture scales three ways:** Base platform charges $55-250 monthly per seat based on town size. Add-on modules like grants management cost $500 monthly. Citizen-facing features price at $1-3 per resident annually, creating multiple revenue streams from single customers. - **Onboarding velocity as competitive moat:** Initial town onboarding took four weeks, now reduced to under two weeks with target of two days. Automation of data ingestion from municipal websites and GIS systems removes manual setup burden and enables self-service for sub-10,000 population towns. - **Revenue milestones misaligned with fundraising:** Investors expect $500K annual run rate minimum for $2-3M seed rounds. At current $95-250 monthly pricing, this requires 50-100 paying towns. Four currently paying customers create significant gap requiring aggressive customer acquisition automation and marketing engine. → NOTABLE MOMENT During a wildfire evacuation debate, Nicole's town council couldn't recall why a specific trail route was rejected five years prior. Her AI instantly surfaced the answer from archived meeting recordings, revealing topography issues and private property conflicts that would have required bridge construction. 💼 SPONSORS [{"name": "Middi Health", "url": "joinmidi.com"}, {"name": "Strawberry", "url": "strawberry.me/unstuck"}, {"name": "CarMax", "url": null}] 🏷️ GovTech, AI Platforms, Municipal Software, Pre-Seed Fundraising

The Pitch

#173 STAG: The Tesla of Construction Equipment?!

The Pitch
44 minInvestor from Flybridge

AI Summary

→ WHAT IT COVERS Adam and Patrick pitch STAG, their electric mini skid steer construction equipment company, seeking $1M at $2.3M pre-money valuation with $1.1M in dealer orders already secured. → KEY INSIGHTS - **Hardware unit economics:** STAG sells electric mini skid steers at $54,900 to dealers with 20% discount, manufacturing cost of $29-30K per unit, generating $12K margin per machine plus attachment and telematics revenue streams. - **Distribution strategy advantage:** Partnering with established multi-location dealers like Bobcat, John Deere, and ASV provides immediate access to existing customer bases, service infrastructure, and national accounts without building costly brick-and-mortar retail operations or direct sales teams. - **Product market validation:** Secured 25 unit orders worth $1.1M across six dealers before production by driving 40,000 miles for in-person demos, proving blue-collar industries require hands-on product testing and relationship building over digital marketing approaches. - **Capital efficiency milestone:** Invested $650K of founder capital to reach production-ready prototype with dealer commitments, requiring only $500K-1M VC funding to bridge six-to-eight months until PO and AR financing becomes viable at scale. → NOTABLE MOMENT Elizabeth Yin initially passed in the pitch room due to hardware cash flow concerns, then requested a follow-up call days later to clarify financing mechanics and ultimately invested $150K after understanding their path to credit lines. 💼 SPONSORS [{"name": "Middi Health", "url": "joinmidi.com"}, {"name": "Strawberry", "url": "strawberry.me/unstuck"}] 🏷️ Hardware Fundraising, Construction Equipment, B2B Distribution, Unit Economics

The Pitch

#174 Investrio: QuickBooks for the People

The Pitch
40 minInvestor from Flybridge

AI Summary

→ WHAT IT COVERS Joyce pitches Investrio, an AI bookkeeping app for solopreneurs making under $100K annually at $20 monthly. Investors pass citing unclear customer segmentation, challenging unit economics, and insufficient evidence of product-market fit despite 500 users. → KEY INSIGHTS - **Pricing constraints limit viability:** Serving solopreneurs earning $65K average annual income at $20 monthly subscription creates unsustainable unit economics. Investors recommend either targeting higher-earning segments willing to pay $200+ monthly or expanding to business-in-a-box solutions capturing more revenue per customer beyond basic bookkeeping. - **Customer segmentation determines success:** Three distinct solopreneur categories exist: side hustlers with minimal revenue, struggling entrepreneurs with non-viable businesses, and serious professionals treating their work as legitimate businesses. The latter group demonstrates willingness to invest in business tools and represents the only sustainable segment for paid software adoption. - **Community-led growth shows early promise:** Building 10,000 social media followers organically and hosting in-person coffee meetups in New York generated 500 users in five weeks post-launch. This authentic community approach demonstrates potential differentiation, though investors question scalability and true customer acquisition costs when accounting for founder time investment. - **Product expansion beyond bookkeeping required:** Successful competitors like Collective, Squire, and Karat serve similar markets by owning entire business stacks including payments, credit cards, employee management, and customer service. Single-function bookkeeping tools cannot generate sufficient lifetime value from lower-income customers to justify acquisition costs and sustain growth. → NOTABLE MOMENT Investors challenged the founder's claim that organic social media growth costs nothing, emphasizing that founder time spent creating content represents real monetary cost that must factor into customer acquisition calculations and overall business viability assessment. 💼 SPONSORS [{"name": "Middi Health", "url": "joinmidi.com"}, {"name": "Strawberry", "url": "strawberry.me/unstuck"}, {"name": "Mint Mobile", "url": "mintmobile.com/switch"}] 🏷️ Solopreneur Finance, Bookkeeping Software, Customer Segmentation, Unit Economics

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