Behind the Scenes: A Year of Tech Startup Stories
Instead of me putting someone else in the hot seat, I’m the one under the spotlight, with Donna St John as my guest host.
Donna and I have known each other for years. She is a marketing leader, a mentor, and someone who knows how to ask the questions that make you pause for a second and give an honest answer. It felt like the right moment to do this, because the podcast has reached that point where it deserves a proper look back. Not a highlight reel, but a real reflection on what the last year has been like, what has surprised me, and what I am taking into the next chapter.
Listen to the Podcast
Available on Spotify, Amazon Music, Apple Podcasts, and YouTube.
How the podcast started, and why I chose this topic
The podcast started as a passion project. I've spent years working with startup founders, sometimes as an employee inside their companies, and more recently through Hey Gabbi, supporting go to market and marketing strategy. Every founder I’ve met has a different story, different backgrounds, different routes into entrepreneurship, different motivations. I kept hearing these stories in fragments across calls, meetings, introductions, and WhatsApp messages, and I wanted the space to dig into them properly. I also wanted to challenge the lazy picture of what a founder is supposed to look like, because that picture is still everywhere.
There is a misconception that founders have to fit a mold, that they need the right network, the right school, the right level of wealth, and often a very technical background. Some do. Plenty do not. The more people I spoke to, the clearer that became, and the more I wanted to share those conversations in a way that felt human, not polished for show.
When I started, I genuinely did not know if I would be able to fill a podcast. I didn’t know how many people would say yes. I didn’t know how long I would keep going. I thought I might do twelve episodes and call it done. Instead, it snowballed.
What surprised me most about the founders I have interviewed
Donna asked me what the common theme is across founders, because on the surface the show is all over the place. Energy tech, MarTech, cyber, HR tech, fintech, and plenty more, with founders from around the world, across ages and backgrounds.
The common thread is passion, every founder I have spoken to genuinely believe in the problem they are solving and that was the biggest surprise. I expected to meet more people who were building purely because they thought the market was hot, or because they wanted a quick exit and a yacht! That has not been the reality, for most of them, there is an emotional connection to the problem. Something they experienced personally, something they saw up close at work, or something that frustrated them enough that they could not ignore it.
That emotional connection does not make the work easier, but it does explain why so many people keep going when it gets hard.
The challenges that keep coming up, no matter the industry
Some challenges are universal, and I see them whether I am interviewing founders, working with clients, or watching startups scale from the sidelines.
There is never enough time, there are never enough resources and there is never enough funding. Even when the world tells us there is plenty of capital available, the reality is more complicated, the investor landscape has shifted. A few years ago, it felt like growth at any cost was the default, throw money at it, hire fast, spend fast, expand fast. Now, investors want to see lean teams, automation, focus, experimentation, and repeatable outcomes. Founders need to be sharper on positioning, clearer on who they are targeting, and more disciplined about what they do next.
I also see more founders doing the work on marketing fundamentals than they used to. Many don’t come from a marketing background, but they are learning quickly, because they have to. The days of vague messaging and wishful targeting don’t last long in a market where attention is expensive and patience is low.
What the podcast has changed for me as a founder
Hey Gabbi is my business, and the podcast has shaped how I think about entrepreneurship in a way I didn't fully expect.
The biggest shift has been this realisation that we’re not alone. Almost everyone I speak to admits they are learning as they go, they have not got it all figured out. They’re building in public, making decisions with imperfect information, and staying humble about what they do not know yet. There’s something oddly comforting in hearing that again and again, because it pulls you out of the spiral that tells you everyone else has a neat plan and you are the only one making it up as you go.
It has also reinforced something I care about deeply, which is that serving customers properly is the whole game. You can spend a fortune on marketing, but the best marketing you can get is a customer who tells someone else what you did for them.
What I have learned about marketing from listening to founders
People are subjected to marketing every day, so everyone feels like they understand it. Most people would not tell an engineer how to do engineering, they wouldn't tell a CFO how to run the books. Marketing does not get the same respect, partly because it is seen as a cost centre, and partly because it is visible, so everyone has a view.
When I work with founders, I start with what they are actually trying to achieve. A founder who wants to raise investment needs a different plan from a bootstrapped founder who needs revenue next quarter. Some want both, and that creates its own tension. Once the objective is clear, we can dig into who they think their audience is, why they chose them, and what evidence they have that there’s product market fit there.
A big part of my role is asking the awkward questions, gently but directly. Why them? Why now? What are you basing that on? What have you tried? What worked. What didn’t? Founders often have a strong instinct about who they should sell to, but instinct is not the same thing as proof, and some of the best stories on the podcast come from founders who realised, sometimes late, that their original target was not the right one.
Marketing is part creativity, part experimentation. There is an art to getting attention, and there is a science to learning what truly resonates, then doing more of it. The harder marketing gets, the more that balance matters.
The constant tension: short term results vs long term brand
One of the most practical parts of the episode was the conversation about juggling immediate demand with long term brand building. Startups need cash flow, if you can’t create momentum and win customers, everything becomes harder. At the same time, if you only chase quick wins, you end up with shallow positioning and no long term story. The way we approach it depends on the model.
If you are selling enterprise, you need to invest early because sales cycles can be long, sometimes twelve to twenty four months. If you are running product led growth, you need to build enough awareness to drive sign ups and trials, then focus on conversion and retention. Either way, the goal is the same, find and retain loyal customers.
It’s about choosing the right customers and keeping them long term, customer acquisition is expensive, keeping good customers, and expanding with them, is where growth becomes sustainable.
When founders should hire, and why timing matters
Donna asked a question I hear in different forms all of the time. “When do you bring in experts? When do you hire? When do you stop trying to do everything yourself?”. The answer starts with having a plan, it doesn't need to be complex, it just needs to exist. Founders wear every hat at the start, sales, marketing, product, hiring, finance, customer calls at all hours. The risk is that success arrives and you cannot handle it.
I’ve seen businesses build momentum, generate inbound, and then drop the ball because they cannot respond fast enough or onboard properly. There’s nothing more painful than telling your team you can’t take any more deals because you cannot service them. It might sound like a dream problem, but it becomes a growth ceiling if you do not fix it quickly.
Hiring is expensive, it takes time and it’s easy to tell yourself you will do it faster alone and sometimes you will. The bigger danger is hiring the wrong person, because that drains time, money, and confidence. The decision often comes down to whether you need a junior hire who costs less but needs support, or a more senior hire who costs more but can take ownership.
This is also where an outsourced function can help, not as a permanent replacement for hiring, but as a bridge until the business is ready for its first marketing hire, and beyond that as the plan evolves.
The biggest change in the podcast, and what I am building towards
When I started, I told myself not to over engineer it and that has stayed true. I record on Zoom, I use AirPods, I’ve had the same mic for years. I have brilliant editors and designers behind the scenes, but we do not try to make it overly polished. We keep the filler words, we keep it human, it’s meant to feel like a real conversation.
I also did not expect listener feedback, I still feel slightly shocked when someone tells me they listen, because I never built the podcast to chase fame or huge numbers. People are listening in twenty seven countries, which is wild, and I am grateful for it, but the point has always been community. I want founders to learn from each other, I want listeners to hear the parts you do not see on LinkedIn, the pivots, the doubts, the messy middle and the reality behind the updates.
One surprise from Season 1 was how hard it was to find female founders. They are absolutely out there, but they are still underrepresented, and their experiences are often tougher in ways that should not still be true. That became a mission for Season 2, and the range of stories has been powerful. Not just for women listening, but for anyone building, hiring, investing, or leading teams. It adds perspective that the ecosystem needs. Looking forward, the big shift is this. I do not want the podcast to be one conversation and done. I want to follow these journeys. As Season 2 wraps up in February 2026, I am going to start revisiting Season 1 guests. Some have raised funding. Some have grown teams. Some have shipped new products. Some have closed and started again. That is the reality of startup life, and it is exactly why the check ins will matter.
One piece of advice I would give new founders
Donna asked me the final question I usually ask my guests. If I had to give one piece of advice, it would be this. Keep doing the things that scare you. Most days as a founder include a moment that feels uncomfortable, a conversation you have not had before, a decision you are not fully ready to make, a room you feel underqualified to be in. Growth lives there, not just business growth, but personal growth, and that is what keeps you moving forward.
Stay curious, keep learning, break out of your usual circle, meet people who do not think like you. If you are commercial, spend time with technical people, if you are technical, learn the commercial fundamentals. The moment you stop learning is usually the moment you stop adding value.
Listen to the episode
If you haven't listened to the episode yet, it is called Behind the Scenes, and it’s a reflection on the first year of Tech Startup Stories, with Donna St John guest hosting and asking me the questions I usually ask everyone else.
Listen to the Podcast
Available on Spotify, Amazon Music, Apple Podcasts, and YouTube.
If you’ve missed any episodes, now is a great time to go back and catch up.
We are taking New Year’s week off, then we will be back with the second half of Season 2, and then Season 3 begins with something I have wanted to do since day one, going back to the founders from Season 1 and seeing what has happened since we last spoke.
