A podcast about what is really like to bootstrap a company! My name is Tiago and I quit my job to focus on building a startup. Join me as I make the mistakes that you can avoid and have conversations with other entrepreneurs from all backgrounds and countries. There are no ads in this podcast! Join our community
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#337 - The Most Misunderstood Path to Wealth and Success
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33:38
In this episode, I dive into my latest thoughts on entrepreneurship, work-life balance, and productivity. I share exciting updates about my project, Podsqueeze, and my collaboration with João on a new product. I discuss the struggle of balancing work with personal life and question traditional metrics of productivity. We also touch on the culture o…
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#336 - In Business Size Actually Matters!!
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33:34
I talk about the importance of prioritizing tasks and managing time effectively. I also discuss my main goal: becoming a better entrepreneur through continuous learning. You'll hear about my marketing strategies, especially focusing on Google SEO, and the challenges of growing a bootstrapped company. Plus, I reflect on the slow growth of Podsqueeze…
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#335 - My Most Embarrassing Mistake Ever
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26:58
I made a mistake with my pricing, but I'm getting over it with some meditation. I'm also excited to go to a podcast conference in London to meet people and learn more. I talked about the importance of understanding business metrics to make good decisions, not just to look impressive. Also, AI is becoming a big deal in our field, and I'm watching ho…
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#334 - Interviewing Rob Walling About How Bootstrappers Get Rich
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1:33:51
Here is my chat with Rob Walling, author of the SaaS Playbook. We delved into product pricing, focusing on value alignment rather than greed, and discussed strategic price increases to reduce churn and bolster marketing. Rob also shared when to start paid ads and how to create impactful content. He offered advice on assembling a team within budgeta…
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#333 - The Pressure of the 30s
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27:18
I've been reflecting on the growth and changes over the past few years. We talked about the leap from a 9 to 5 to full-time entrepreneurship, the societal pressures we face, especially as we hit our 30s, and the quest for work-life balance. I also pondered the idea of renting an office space to combat the solitude of working from home and to build …
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#332 - Money, Time and Fun - You Can Have It All!
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26:22
In today's podcast, I dive deep into how we juggle our time, chase wealth, and strive for that elusive work-life balance. I shared some personal stories, including the ups and downs with my own project, Podsqueeze, and how I'm tackling growth challenges head-on. We also talked about why we leave cushy jobs to strike out on our own—is it for freedom…
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#331 - The Tool That Most Companies Use But Don't Want You To Know
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24:01
I'm happy to share some personal updates and entrepreneurial insights. Lately, I've discovered Apollo, a networking tool that's completely revolutionized the way I connect with others. Our Website was completely down for a complete 30 min and I have never beens this stressed XD And to continue this stressing week we decided to increase Podsqueeze p…
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#330 - Top Productivity Hack Every Entrepreneur Must Know!
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22:48
I dive into the nation's burgeoning immigration scene, exploring its cultural boons and economic hurdles. As a business owner, my political perspectives are ever-shifting, particularly concerning taxes and government policies. Plus, I'll reveal my journey towards achieving a work-life balance and heightened productivity, inspired by "The 4-Hour Wor…
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#329 - How Daniel Invests His $500K ARR Portfolio
1:26:54
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Hey fellow indie hackers, just wrapped up a super cool chat with Daniel, a 26-year-old entrepreneur who's totally killing it with a $500k SaaS portfolio. He and his brother started young, sold their first company, and now they're smartly reinvesting into more SaaS, real estate, and other assets. Daniel's all about that cautious growth and avoiding …
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#328 - The Book That Every Maker Needs To Read
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25:08
Hey fellow indie hackers! I've promised myself (and you guys!) that from now on, I'll drop a fresh episode every Monday – gotta keep that trust going, right? I also dived into my new adventure with PodSqueeze, chatting with customers on the podcast and soaking up all their amazing insights. Oh, and I had this awesome talk with Rob Walling, which le…
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#327 - Why Some Products Grow And Others Don't?
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20:42
Why do some products grow more than others? In today's episode of "The Wannabe Entrepreneur," I ponder over the growth trajectory of my product, the inevitable plateau, and the significance of early adopters and the early majority. I confess to overlooking long-term marketing tactics initially and discuss strategies to break into fresh markets, lik…
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#326 - You Need To Grow Together With Your Business
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22:50
I'll talk about the crucial skill shifts, strategies to keep customers, the art of delegation, and the power of SEO and email marketing. Learning from fellow entrepreneurs has been key, and I'm eager to show that bootstrapping can lead to serious financial wins. Links Support This Podcast DM me on Twitter Join The WBE Community Try PodSqueeze Times…
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#325 - Don't Waste Time... Pay For A Marketing Expert Instead!
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26:12
Ever wondered how a developer turns into an entrepreneur? In this episode of "The Wannabe Entrepreneur," I, Tiago, dive into my own transformation, revealing the ins and outs of my entrepreneurial journey. I'll walk you through the crucial role of passive user acquisition strategies, such as SEO and content creation, and explain why it's essential …
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#324 - Starting a Podcast in 24 Hours: Guerrilla Marketing 101!
29:08
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29:08
Are you ready to dive into the world of guerrilla marketing and podcasting? I'm Tiago, the host of "The Wannabe Entrepreneur" and co-founder of PodSqueeze. In this episode, I'm excited to share our marketing focus for early 2024 and the behind-the-scenes of our rapid-fire podcast creation, "Lessons from a Podcaster." I'll walk you through our launc…
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#323 - The Crazy Journey from $0 to $100K in One Year!
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56:02
In this episode, together with my co-founder João, we dive into our entrepreneurial rollercoaster with Pod Squeeze. From the ashes of a failed project to the thriving business we run today, we're peeling back the curtain on our journey. We'll chat about the crucial role of user feedback, the exhilarating boost from financial wins, and the gritty de…
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#322 - Startup Plateau and Conquering the Early Majority
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18:51
Are you an entrepreneur facing challenges and feeling frustrated with the stagnation of your company? In this episode, I, Tiago, the host and co-founder of Podsqueeze, share my own experiences and insights. Despite the difficulties, I realize that our achievements are impressive. I discuss a conversation I had with a Portuguese entrepreneur and inv…
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#321 - How to go from $100K to $1M with My Indie Business?
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29:10
In this episode of "The Wannabe Entrepreneur," we will be exploring a range of topics. I will start by discussing the challenges of buying a new home and the art of gift-giving, sharing my personal experiences. Then, I will delve into the world of influencer marketing and compare working cultures in Portugal and Germany. I will express my frustrati…
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#320 - Interviewing Andrew Gazdecki About How To Sell a Bootstrapped Startup
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Have you ever wondered about the process of selling startups? In this podcast episode I had the pleasure of interviewing Andrew Gazdecki, the founder of Acquired.com. We dive into his experience of scaling his company and the significance of having a distribution mindset and a strong team. Join us as we explore the importance of delegation, hiring …
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#319 - From Cheating at a Podcast Festival to Sponsoring It
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24:06
Let me take you on a rollercoaster journey through my experiences. This week, I've experienced both the highs and lows of this exciting world of indie hacking. Join me as I share the challenges of running PodSqueeze and managing co-founder relationships. I will also speak about our most recent sponsored event and gaining recognition in the Portugue…
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#318 - How Makers Take the Most Out Of a Tech Conference
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24:02
What it's like to attend a major tech conference like the Web Summit? Well, in this episode, I'll be sharing my personal experiences from the event. Despite all the controversy and big tech companies dropping out, the turnout was massive! I'll be discussing my networking strategies, like using the event app to connect with people and finding a quie…
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#317 - This Was Probably My Biggest Mistake Ever
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27:02
Have you ever made a critical mistake that had a significant impact on your business? In this episode, I'll be sharing my own experience as the co-founder of Podsqueeze. Blocking the upload feature to combat fake accounts seemed like a good idea at the time, but it ended up causing a decrease in user engagement and revenue. I'll be discussing the i…
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#316 - Interviewing Dagobert About How to Avoid Burnout as a Founder
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1:36:52
Have you ever experienced burnout and its impact on your health? Well, Dagobert shares his personal experience with burnout and how it led to a significant shift in his work-life balance. We also dive into the importance of therapy for mental health and how it played a crucial role in Dagobert's recovery. Links Follow Dagobert's Twitter Join The WB…
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#315 - How to Sponsor a Conference with your Indie Business
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30:38
Have you ever sponsored a conference to grow your business? In this episode, I, an indie maker, and my co-founder Joao, dive into our experience sponsoring a conference in Berlin for our company, Podsqueeze. We were initially worried about being scammed, but we ended up sealing a sponsorship deal for $700. I chat about the perks of attending such e…
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#314 - Interviewing Daniel about the Ups and Downs of Building Wundertax
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1:13:34
I am interviewing Daniel, the CEO of Wundertax. He takes us on a journey from Hong Kong to Germany, sharing his experiences in entrepreneurship and the creation of Wundertax. We dive into the challenges of starting a business, securing funding, and navigating co-founder dynamics. Daniel also shares insights from his time in Amsterdam and how Wunder…
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#313 - This Is Going To Be a Huge Marketing Bet
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14:04
I have some exciting news to share - our company has decided to sponsor a podcasting conference in Berlin as part of our marketing strategy. I'll be discussing our experimentation with different approaches like cold emails and automation, as well as our current focus on sponsoring conferences. Join me as I talk about my goals for attending the conf…
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#312 - How To Hire Top Freelancers for Your Indie Company
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19:33
Have you ever wondered what it's like to hire new team members for a bootstrapped company? Well, in this episode, I'll be sharing my personal experience with hiring for my company, PodSqueeze. It all started when I hired a content agency to write ebooks, which turned out to be a success. But when we needed blog posts for SEO, we reached out to them…
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#311 - The Most Uncertain Times: Navigating the Ups and Downs of PodSqueeze
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10:42
I'll be reflecting on the ups and downs of our journey so far, including the initial success and growth of our company. But I also have concerns about the market and AI trends. I'll be sharing my three conditions for deciding whether to continue with PodSqueeze, and expressing my unwavering passion for this project. Oh, and I'm thrilled to announce…
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#310 - How To Legally Create an Indie Company and Minimize Taxes
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41:26
Have you ever wondered what it takes to set up your own company? In this podcast episode, I share my personal journey of starting UserQuest and the obstacles I encountered along the way. One of the biggest challenges was finding accountants who truly understood my software-as-a-service business model and the complexities of taxation. It was frustra…
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#309 - Tips for Indie Makers Perform at The Highest Level
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32:34
Are you an indie maker looking to perform at your best? In this episode, I dive into strategies for reaching the highest level of productivity. Discover the power of structuring your day and finding a routine that suits you. As a fellow night owl, I emphasize the importance of working with your natural body and brain rhythms. Plus, I reveal the ben…
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#308 - Interviewing Taylin Simmonds Founder of Ghostlii
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46:29
I had the pleasure of interviewing Taylin Simmonds, the co-founder of Ghostlii, a content marketing agency. Have you ever wondered how to find success as an entrepreneur while staying true to your artistic vision? Well, Talyn shares his incredible journey as an indie maker and entrepreneur, exploring the fascinating intersection of art and business…
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#307 - What I wish I’d known when I started Indie Hacking
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41:26
Have you ever wondered how to navigate the world of indie hacking? Well, today I'll be discussing the importance of learning and experimenting in indie hacking, the significance of having a financial runway, and the need to prioritize mental health. We'll also explore the audience-first approach, finding product-market fit, and the importance of ti…
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#306 - I Don't Know How To Run A Business
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25:00
In this episode, I, Tiago, an indie maker and entrepreneur, share my journey and the challenges I face in navigating the business side of things. From setting up a company to handling taxes and hiring professionals, there's a lot to learn. I discuss the lack of discussion around these less glamorous aspects and the fear of making mistakes. I also s…
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#305 - How Success Changes The Way You See Yourself
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31:33
Have you ever wondered how success can change a person? In this episode, I'll be reflecting on this concept, and using I'll be sharing my own experiences with success through my company, PodSqueeze. From childhood dreams of being an entrepreneur to taking my profession seriously, I'll discuss the impact success has had on me. We'll also touch on th…
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#304 - Don't do business with people you don't trust
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17:28
In this episode, I'll be sharing my recent experiences with my business partner and landlord. From struggles with onboarding business partners who seemed to take control of the conversation, it's been quite a journey. I'll also be discussing my personal experience with our rented flat in Lisbon. Join me as I reflect on these experiences, contemplat…
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#303 - Interviewing Tony Dinh on how to run a successful indie businesses
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45:08
In this podcast episode, Tiago interviews Tony Dinh, a successful indie hacker, about the challenges and goals of running an indie company. They discuss their own experiences and the importance of finding the right co-founder. They also talk about the different phases of being an indie hacker and the goals that come with each phase. Tony shares his…
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#302 - My Company is Making $10K Per Month
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28:08
Is money a synonym for success? I'm thrilled to announce that we've reached a milestone of $10,000 in revenue. Plus, I recently bought a used car and the response on Twitter was amazing. Join me as I discuss the importance of freedom over money for indie makers and explore a potential product idea for a search engine for podcast episodes. I'll also…
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#301 - Why Do We All Live The Same Life?
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29:48
Have you ever wondered about human achievements, societal norms, and different lifestyles? Today, I'll be reflecting on these topics, specifically in the context of indie hacking. I'll also share my thoughts on two inspiring documentaries that showcase individuals living extraordinary lives, and question why society often discourages deviating from…
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#300 - Sailing Against the Tide
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20:06
Have you ever participated in a quiz with friends and suddenly realized how little general knowledge you actually have? That's exactly what happened to me recently. So, I've decided to study flags to improve my knowledge in that area. On another note, I'm really passionate about sailing, but navigating the strong tides and currents of the river in …
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#299 - Podsqueeze just hit $100,000 in annual revenue!
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27:54
Hey there! Have you ever wondered what it's like to reach a major milestone in your startup? Well, in this episode, I'm excited to share with you the recent achievement of my own startup, Pod Squeeze, hitting $100,000 in annual revenue. But it's not all smooth sailing. I'll be diving into the challenges we faced, including a decline in monthly recu…
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#298 - Our MRR is Going Down 😱
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33:59
In this episode of my podcast, "Wannabe Entrepreneur," I share some valuable insights on the challenges and realities of being an indie hacker. As an indie hacker myself, I understand the importance of finding a balance between financial stability and pursuing your passion. I discuss the need to sometimes take on freelance work to make ends meet an…
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#297 - Interviewing Yossi and Simon About TinyKiwi Acquisition
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1:15:57
Have you ever wondered what it's like to sell or acquire a company in the indie scene? In this podcast episode, I had the pleasure of interviewing Simon, the founder of Feedhive, and Yossi, the founder of Tiny Kiwi, as they discuss the acquisition of Tiny Kiwi by Feedhive. We delve into the process of selling and acquiring a company in the indie ma…
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#296 - We are getting on each other's nerves...
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29:14
Have you ever wondered if remote work is as productive as working from an office? In this podcast episode, I, Tiago, an indie hacker and entrepreneur, share my experience with remote work and the benefits of working from a co-working space with my co-founder, João. I believe that remote work can be productive, but it depends on the type of work and…
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#295 - Can I Build a Successful Company Only by Bootstrapping?
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40:05
Have you ever started a company and had to pay taxes? In this episode, I, Tiago, the host of "Wannabe Entrepreneur", share my personal experiences of setting up a company in Portugal. I talk about the challenges I faced with the complicated tax system and how I found ways to reduce the taxes my business had to pay. I also reflect on the decision of…
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#294 - Can Millennials Really Accomplish Anything They Want?
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34:54
Have you ever wondered what the millennial generation is capable of achieving? In this episode of "The Wannabe Entrepreneur," I discuss the potential of millennials to accomplish great things and the importance of pursuing our dreams. I also share personal stories about a volleyball game and my experience working at a co-working space in Lisbon. Ad…
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#293 - Living Life on My Own Terms
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33:56
Have you ever felt like you're living life on someone else's terms? In this episode, I'll be discussing some important topics, including societal biases around gender roles, my journey as an indie hacker, and my idea of sharing profits with partners who believe in a company. I'll also be reflecting on the challenges of being a leader without a clea…
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#292 - The Good, The Bad, and The Spammy: My 2023 Cold Email Guide
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38:48
Have you ever wondered how technology and communication have evolved over the years? In this episode of "WBE Entrepreneur," I reflect on this topic and share my insights on the effectiveness of cold emailing. I discuss how my cold email strategy has contributed to the success of my current venture, Podsqueeze, and share my recipe for a successful c…
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#291 - I am taking the fight to a whole other level
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31:24
Have you ever started something from scratch and worked your way up? As someone who practices Muay Thai, I can attest to the importance of gradual improvement in both martial arts and entrepreneurship. In this episode, I'll be sharing my personal experience and how it relates to building a business. I'll also be discussing my financial goals for Po…
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#290 -To AppSumo or Not to AppSumo. What shall we do?
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26:54
What should you consider when negotiating a deal? In this podcast episode, I share my experience playing football in Portugal and how owning a ball made me popular among my friends. I then dive into my business, PodSqueeze, and the process of finding the right transcription service. João and I tested various services and found a partner that reduce…
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#289 - Everything Is Changing And I Like It
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34:01
Have you ever felt lost in your career journey, unsure of what job you truly love? In this episode, I share my personal journey through different jobs and how it led me to my current project, Podsqueeze. I reflect on my experiences working at Trivago and Weekend, and how they shaped my perspective on entrepreneurship. As I continue to grow and deve…
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#288 - Hey, have you heard about the power of ProductHunt?
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31:36
Have you ever wondered what it takes to launch a successful product on Product Hunt? Well, let me tell you about my experience with launching my own product, Podsqueeze. As the founder, I understand the importance of optimizing processes and conversion rates before launching on ProductHunt. In this podcast episode, I share my journey of scaling up …
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