Podcast

Ryan Hayward on Storytail: Building a Live Content Platform for the Next Generation of Experienced Creators

In this episode, Steve and Ryan Hayward, Co-Founder of Storytail, explore the challenges of product-market fit and effective storytelling.

by hao-nguyen on July 23, 2023

About the guest

Ryan Hayward

Co-Founder at Storytail

Ryan Hayward is a designer-turned-founder who started freelancing at 14 and launched his first business, Pitch Proof, at 17. He ran Australia’s first online virtual design conference in 2019, before COVID, and the experience of building interactive live events became the foundation for Storytail, an online platform that helps experienced creators deliver interactive, two-way live content without the fatigue of standard video meeting tools.

Episode overview

Ryan Hayward, co-founder of Storytail, joins Steve Grace for a conversation about building a live content platform from scratch, what he has learned about communicating a product people need to experience before they understand, and why his co-founder taught himself to code while they were building the product. The episode is an honest account of the early product-market fit phase, the private beta, and what Ryan wants to accomplish in the year ahead.

From design freelancer at 14 to online events pioneer

Ryan started doing graphic design gigs online at 14, without thinking of it as a business. He then built Pitch Proof, a software platform for designers to present logos to clients, which evolved into a content business with a sizeable social following. In 2019, before COVID and before most people thought about virtual events, Ryan ran Australia’s first online virtual design conference, attracting 400 live viewers on YouTube in a 10pm to 3am streaming session. The event planted the seed for Storytail.

“The first online virtual design conference blew up and that was just the craziest experience I’ve ever had. That’s when storytail sparked any sort of interest in terms of being like an online event space that I wanted to enter.”

Ryan Hayward 6:00

What Storytail solves: two-way live content

Standard live streaming, going live on Instagram or running a webinar in Zoom, is a one-way experience. The creator talks at an invisible audience and receives almost no feedback. Storytail is built around what Ryan calls breaking the screen: making live content interactive through mirror boards, whiteboards, forms, and real collaboration tools embedded directly in the delivery environment. The target user is not a social media content creator but what Ryan calls an experienced creator: someone who wants to teach, run masterclasses, or build genuine relationships with their audience through live interaction.

“People don’t want to just consume content, they actually want to engage with it and create a deeper level of engagement. When you do that you unlock a new level of trust and relationship with your audience.”

Ryan Hayward 9:00

Private beta, product-market fit, and the communication challenge

At the time of the episode, Storytail was 12 months into development and had about 100 private beta users. The team had built multiple versions of the platform and were still working through how to communicate what the product does to the right audience. Ryan describes this as their single biggest challenge: the platform is powerful but requires the right use case framing to land. One of their beta users was a major hardware retailer whose use case Ryan did not anticipate, suggesting the platform may find its most impactful applications in unexpected places.

Planning a seed round and the year ahead

Storytail had not taken external funding at the time of recording. Ryan was planning a seed round in early 2024 and had already begun warming up investors throughout the prior year. His goals for the next 12 months: secure the seed round, launch publicly, begin monetising, and build out the product features users were already requesting. His co-founder Tom had taught himself to code from scratch during the 12 months of building Storytail, which Ryan credits with removing a key constraint that stops most non-technical founding teams.

Key takeaways

Start before you know what it is called. Ryan began freelancing at 14 without knowing the word entrepreneur. The path from design gigs to a software company to a live content platform followed his genuine curiosity and passion, not a planned career trajectory.
Two-way live content is fundamentally different from one-way broadcasting. The Zoom fatigue and one-way streaming problem are real. Storytail’s differentiation is building collaborative, interactive layers into live content delivery, which changes the relationship between creator and audience entirely.
Product-market fit communication is as hard as the product itself. Ryan’s team built a powerful platform but spent the first year figuring out how to describe it to the right person. This is one of the most common and underestimated challenges at the early stage: having a working product and not being able to explain it.
Warm investors before you need them. Ryan spent a year having investor conversations without asking for money, building familiarity and trust before the official seed round. This compresses the raise timeline and reduces the cold-pitch problem significantly.
A co-founder who can learn anything is more valuable than one who already knows everything. Tom, Ryan’s co-founder, did not know how to code 12 months before the episode. He learned to build the platform from scratch. The ability and willingness to learn fast under pressure is the most transferable early-stage skill there is.

Mentioned in this episode

Frequently asked questions

What is Storytail?

Storytail is an online platform for delivering live content in an interactive, two-way format. It is designed for experienced creators: people who want to run masterclasses, webinars, and live sessions with genuine audience participation, rather than broadcasting one-way to an invisible audience on standard video meeting or streaming platforms. The platform includes tools like mirror boards, whiteboards, forms, and collaborative features that allow creators to break the passive consumption dynamic of typical live streams.

Who is Storytail designed for?

Storytail’s target user is what Ryan calls an experienced creator: someone already creating content online whose intention is to teach or enable their audience to learn, not just to be consumed. They want to run live content that builds genuine relationships and unlocks a deeper level of trust with their audience. Early beta users included educators, coaches, and one major retail hardware brand that found an unexpected use case for teaching practical skills to customers.

How did Ryan Hayward get into entrepreneurship?

Ryan started doing graphic design gigs online at 14 years old, without thinking of it as entrepreneurship. He followed his passion for design and monetised it naturally. At 17 he built his first formal business, Pitch Proof, initially a software tool for designers presenting logos, which evolved into a content brand with a large social following. Running Australia’s first online virtual design conference in 2019 with 400 live viewers was the moment that led directly to Storytail.

Has Storytail raised any funding?

Storytail had not taken external funding at the time of the episode, having bootstrapped through the 12-month R&D and private beta phase. Ryan was planning a seed round in early 2024 and had been warming investors throughout 2023 without a formal raise. He viewed the public launch, early monetisation, and seed round as the key milestones for the 12 months following the episode.

What has been the hardest part of building Storytail?

Ryan identifies communicating what the product does to the right audience as the single hardest challenge. The platform is powerful but requires the right framing to resonate with potential users. The team iterated through two or three different positioning approaches while keeping the core vision consistent. Ryan says they were getting close to the messaging that was landing clearly at the time of the episode, and that each new conversation added to their understanding of exactly who the product is for and how to describe it.

Topics discussed

Live contentCreator economyOnline eventsInteractive platformsZoom fatigueEarly-stage startupsProduct-market fitSeed fundingSaaSDesign entrepreneurship

Full transcript

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Show full transcript (21 minutes, 7 sections)

0:00 Introduction

Welcome to the show. Thanks for having me, it’s nice to be in a different studio today. You’re the founder of Storytail. I know nothing about Storytail and nothing about you so I’m going to learn along with the audience. Give us a very quick synopsis. Storytail is an online platform for people to deliver their live content differently. Everyone’s Zoom fatigued, we’ve had the pandemic, and Storytail is our fresh solution. We’re helping a new generation of creators to actually deliver content differently, so they can engage and make their content worthwhile.

4:00 Two-way versus one-way content

There are one-way conversations and two-way conversations. Your typical live stream going live on Instagram, talking to what says 30 people watching you, is very awkward with no feedback. We’ve hacked together our own event platforms since before the pandemic. But it was very much a one-way conversation. One of the big things we focus on with Storytail is how you can actually deliver content by what we call breaking the screen: creating two-way conversations and getting people interacting. Mirror boards, whiteboards, forms, actual collaboration. People don’t just want to consume content, they want to engage with it and build a deeper level of trust.

7:00 Ryan’s background in design and Pitch Proof

My background’s in design. Even before I knew what entrepreneur meant I was doing graphic design gigs online and built a freelance business at 14. I started Pitch Proof at 17, initially a software tool for designers to present logos to clients online, which evolved into a content business. We grew a large social media following. In 2019 we held the first online virtual design conference even before the pandemic. Australia is a terrible time zone so we ran from 10am to 3am and had 400 people live on YouTube. That was the first time Storytail sparked any real interest as an online event space.

11:00 What Storytail is and who it is for

We call our target users experienced creators. Not just people who create social media content to be consumed. They want to run masterclasses, webinars, and live video content that builds deeper relationships. They’re already creating content online. Their intention is to teach or for people to actually learn. We’re designed for them, not for video meeting platforms. We’re seeing a new vertical of creators forming who want genuine engagement, not just a thumbs up emoji in the chat.

14:00 12 months of R&D and the private beta

We started Storytail about 12 months ago. We’ve done a lot of research and development, built a couple of different versions, and we’re now in private beta with about 100 users. We’re working closely with them to master their use cases before we do a public launch and introduce pricing. One of the users is a major retail hardware brand, which I never would have predicted. The concept of being able to teach whether practical or theoretical is opening up use cases I didn’t anticipate.

17:00 The communication challenge

Our biggest problem the past 12 months is how to communicate about our product to the right people. We’ve told the story in two or three different ways. The vision has stayed the same but the communication has been different. I think we’re finally starting to get to the stage where what we’re saying is landing with people. My co-founder Tom didn’t know how to code 12 months ago. He’s very tech-switched on and just jumped in and learned on the go. That’s been a huge plus because we can build without being constrained by money.

20:00 Seed round and goals for the year ahead

We’re coming into a seed round early next year. We’ve been talking to investors and VCs throughout this year to warm them up. The biggest goals for the next 12 months: unlock the seed financing, roll out publicly, get people using it regularly, start to monetise, and build out the product features we know users want. I want to enable people to do their best work in the way that suits them, not nine to five. That’s what I’ve always wanted as a founder and it’s what I want to give to everyone who joins us.

About the host

Steve Grace is the founder and CEO of The Nudge Group, a technology-focused recruitment and advisory business. He has built and scaled companies across Australia and the US, and hosts Give It A Nudge to spotlight founders and operators building something meaningful.

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