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Exploring Creative, Non-traditional capital strategies
In this episode, I'm joined by Aakash Shah, founder and CEO ofWyndly, a healthcare startup revolutionizing allergy treatment. Akash shares his journey from personal allergy sufferer to innovative healthcare entrepreneur and reveals how he navigated the choppy waters of fundraising without relying solely on traditional venture capital.
If you're interested in creative capital strategies, Akaash demonstrates how startups can thrive by thinking outside the VC box. Learn how he leveraged customer relationships and learned finance lessons from restaurant owners that got Wyndly where it's at.
Aakash Shah leveraged his personal experience with severe allergies to create an innovative, accessible solution for allergy sufferers. With a background in software and growth/product, Aakash is committed to ridding the world of allergies forever.
After graduating from the University of Virginia in 2016 with a dual major in Computer Science and Cognitive Science, Aakash joined small technology companies, knowing that technology would continue to change the world. Now, as a Wyndly patient and founder, he's dedicated himself to fixing people's allergies with personalized treatment and phenomenal care.
His journey from Y Combinator to exploring alternative funding strategies offers a fresh perspective on startup growth and capital acquisition in the healthcare sector. Aakash's approach combines his tech background with a deep understanding of healthcare needs, creating a unique blend of innovation and practicality in the allergy treatment space.
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Aakash Shah (Wyndly) onYC, Angels & Runway Tactics
Guest: Aakash Shah, Founder & CEO of Wyndly (telehealth allergy practice).
Core topic: Fixing environmental allergies at the root via at-home testing and immunotherapy; never rely on daily antihistamines again.
Founder journey: Personal allergy struggle → partnered with physician co-founder → YC acceptance → scaled to all 50 states.
Fundraising lessons: YC as credibility & momentum engine; market cycles matter (2021 vs. 2023); target aligned investors; keep processes tight.
Capital strategy: Annual prepay, vendor terms, revenue-based financing, and negative cash conversion cycle to extend runway.
Advice: Build a founder support circle; use venture as an option—raise from customers when you can.
Full Transcript
Jason Kirby: Hey everyone, welcome back to Fundraising Demystified. Today we have Aakash Shah with us, founder and CEO of Wyndly. Welcome to the show.
Aakash Shah: Thanks so much for having me, Jason. I really appreciate the opportunity.
Jason Kirby: I'm excited to have you on the show. You're solving a big problem that affects probably billions of people when it comes to allergies. Tell the audience a little bit about you and what you're building at Wyndly.
Aakash Shah: Absolutely. I run Wyndly, and what we do is fix allergies—forever. We start with what you breathe: if spring pollen or dust wrecks you, we can take care of you long term so you never have to rely on daily antihistamines again. This is personal for me—I was a terrible allergy sufferer from college into my first job. I couldn’t breathe and thought it was normal. Like many twenty‑somethings, I ignored it… and I’m paying for it now that I’m older. Eventually I sought out an allergist and the journey was a labyrinth. When I finally got care, the answer was weekly shots for years. That didn’t fit my life. I found a fully compliant alternative, realized incentives—not science—were blocking access, and dedicated myself with my co‑founder to getting the best allergy solution into people’s hands regardless of our healthcare system’s quirks.
Jason Kirby: This hits close to home. I grew up in Southern California with no allergies, moved to New York and suddenly couldn’t breathe—windows open at night meant waking up congested. Sprays helped a bit. I’ve since moved to London and it’s milder, but allergies run in my family. My mom gets shots multiple times a year. Big, painful problem—so investors get excited. Before fundraising, though, you’ve got a product and engineering background. How did you move from that to a personalized healthcare business?
Aakash Shah: The short answer: I had the problem, solved it for myself, then asked, “How do we do this for more people?” First my wife, then my sister‑in‑law. After proving efficacy with three people, I looked for a market. My background is growth product—using engineering to grow a business—so it was a natural fit for a consumer problem. My co‑founder is a physician, so he’s our technical founder in the medical sense. It’s easier than ever to stand up software; medicine isn’t easier. Founders should pick a big problem that fits their skills and lean into strengths.
Jason Kirby: And you’ve had prior founder experience?
Aakash Shah: In college I built a study tool because I hated studying. First lesson: customers often say one thing and want another. Students said they wanted to study more; really they wanted better grades. We pivoted to test bank review and it worked, but access vanished after graduation, so we wrapped it up.
Jason Kirby: Fast‑forward to Wyndly. You raised a couple million—walk us through the strategy, timeline, and experience.
Aakash Shah: We knew the product worked—I started the company with the doctor who helped me. Wyndly is an allergy practice that fixes breathing allergies forever, delivered online and made simpler than any doctor visit you’ve had. We ship an at‑home test, learn your triggers, ship your meds, and you can text, email, or call us directly—no phone trees. My doctor was in Denver while I was in New York, so he already knew how to handle non‑traditional care. After fixing me and my wife, we validated demand: would allergy sufferers try fixing it online? After about 20 signups we felt pull. We planned to self‑fund from day jobs, but applied to Y Combinator as a test of co‑founder seriousness—and got in. YC provided our pre‑seed; that capital is enough to prove most ideas.
Jason Kirby: How did YC change things afterward?
Aakash Shah: YC was incredible. Day one they said: we’ll give you money, connections, docs, and access to brilliant people—it’s on you to use it. Some needed structure and struggled; others rocketed. YC helped us go from a single‑state practice to 50 states in ~3 weeks because doors opened. Demo Day concentrates demand; trying to recreate that pressure later is hard. Many early angels started as patients—we fixed them, then they invested. Timing matters too.
Jason Kirby: You raised again around 2023—how was that different from 2021?
Aakash Shah: In 2021, healthcare interest was high and rates were low. In 2023, rates rose and attention shifted. We leverage AI but we’re a healthcare company, not an AI company, so generalist appetite was lower. The lesson: target aligned investors; understand cycles. Get to fast “no’s” to protect focus—don’t pitch B2B infra funds if they don’t do consumer healthcare.
Jason Kirby: Tactically, how did you get that many meetings and close the round?
Aakash Shah: We announced in early 2023 after running a process in late 2022. I keep an open investor update list—conversations become distribution. When you finally say “we’re fundraising; here’s a term sheet; we’re closing X,” people who’ve followed along can lean in. Relationships compound. Demo Day heat fades, but trust you build persists.
Jason Kirby: What would you do differently—biggest frustrations?
Aakash Shah: Hearing hundreds of no’s hurts and can sap momentum, which lengthens the fundraise and pulls you from the business. Keep it tight: time‑box the raise (e.g., 90 days), then reassess. Venture is an option, not a lifeline. If the run stalls, find other ways to grow.
Jason Kirby: Let’s talk capital strategy. How do you think about financing a non‑SaaS healthcare business?
Aakash Shah: Early you sell equity—no customers, no revenue means no debt. Later, with revenue, use tools normal businesses use: loans, revenue‑based financing, factoring, vendor terms, price changes, or annual prepay. Talk to operators in harder businesses (clinics, restaurants, CPG) to learn cash discipline. Our biggest runway win was introducing an annual plan—12 months paid upfront. Cash today lets you operate and makes you more attractive for future raises.
Jason Kirby: And mind the cash conversion cycle—ideally negative. Credit card float, vendor terms, and payout timing help a lot.
Aakash Shah: Exactly. Align payout timing (like sales bonuses) with collections; avoid paying out before cash is in. Structure operations to collect earlier and pay later—ethically and transparently.
Jason Kirby: Parting advice?
Aakash Shah: Find your people. A founder support group to learn with, celebrate with, and commiserate with gives you energy to take 300 no’s and keep going. And avoid fundraising if you can—raise from customers first.
Jason Kirby: Every business is different; fundraising may be necessary to reach your goals, but options expand when you run a tight capital strategy. Akash, where can people learn more?
Aakash Shah: Wyndly is at wyndly.com (W‑Y‑N‑D‑L‑Y). We’re on YouTube, TikTok, and Instagram. Personally, email me at akash@wyndly.com or connect on LinkedIn.
Jason Kirby: We’ll link everything in the description. Thanks for joining us on the pod today.
Aakash Shah: Thanks for having me.
FAQ
What is Wyndly’s treatment approach?
At-home allergy testing identifies triggers, followed by physician-guided immunotherapy that treats root causes so patients can reduce or eliminate daily meds over time.
How did YC help Wyndly scale nationwide?
YC provided capital, credibility, mentors, and intros to licensed physicians, enabling Wyndly to expand from one state to all 50 in a matter of weeks.
What are practical capital strategy levers for founders?
Annual prepay plans, revenue-based financing, vendor payment terms, credit card float, and disciplined cash conversion cycles—plus targeting the right investors for your stage and sector.
Is Wyndly an AI company?
Wyndly uses AI where helpful, but it’s a healthcare practice focused on patient outcomes, not an AI product company.
