• #335 - My Most Embarrassing Mistake Ever

    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 how it affects mental health support.

    Links

    Tiago's Twitter

    Try Podsqueeze

    Support This Podcast


    Traveling and Excuses (00:00:12)

    Tiago shares his recent travels and acknowledges the delay in posting episodes.


    Patreon Support (00:01:21)

    Tiago thanks patrons for supporting the podcast and encourages additional contributions.


    Growth Mistake (00:02:24)

    Tiago recounts a mistake in pricing strategy that impacted the company's growth.


    Meditation and Anxiety (00:08:05)

    Tiago discusses the benefits of meditation in managing anxiety and maintaining focus.


    Metrics and Market Analysis (00:09:15)

    Tiago emphasizes the importance of tracking various metrics and understanding market dynamics.


    Reviewing and Decision-making (00:13:20)

    Tiago advises reviewing metrics at intervals and making decisions based on accumulated data.


    Podcasting Conference (00:16:35)

    Tiago shares his excitement about attending a podcasting conference in London and the potential industry insights.


    AI and Ethics (00:21:11)

    Tiago reflects on the use of AI in community engagement and discusses ethical concerns related to AI as a therapist substitute.


    AI and the Future (00:22:10)

    Discussion on the potential future of AI, including AI friends, partners, and its impact on content creation.


    AI in Content Creation (00:23:17)

    Exploration of using AI in video creation, referencing a successful young YouTuber and the potential of AI-generated scripts.


    Learning from Young Entrepreneurs (00:24:26)

    Observations on the use of AI by young entrepreneurs and the potential for learning from their experiences.


    Considering Consultation (00:25:28)

    Contemplation of seeking consultation from a successful young YouTuber for insights into algorithms and content creation.


    Upcoming Trip to London (00:26:39)

    Mention of an upcoming trip to a podcasting conference in London and a sign-off for the episode.

    26m - May 21, 2024
  • #334 - Interviewing Rob Walling About How Bootstrappers Get Rich

    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 budgetary limits and revealed that smart business structuring can lead to profit with less work. Our conversation ended on the importance of joy in entrepreneurship, emphasizing freedom, purpose, and relationships.

    These shownotes were created with Podsqueeze

    Links and Mentions

    SAS Playbook: 01:31:58

    Startups for the Rest of Us Podcast: 01:31:58

    MicroConf YouTube Channel: 01:31:58

    The Zen Founder Guide to Founder Retreats: 01:30:39

    Twitter Thread for Book Recommendations: 01:32:37


    Timetsamps

    Rob Walling's Book (00:01:16)

    Writing the Book (00:02:13)

    Pricing Strategies (00:06:36)

    OpenAI's Pricing Strategy (00:11:54)

    Competitive Pricing Strategy (00:13:50)

    Greed and Motivation (00:16:40)

    Reasons for Raising Prices (00:17:50)

    Impact of Pricing on Marketing (00:19:24)

    Paid Advertising Considerations (00:20:59)

    Using Ads for SEO Strategy (00:24:57)

    Marketing Approaches for SaaS (00:29:50)

    Creating Compelling Content for Reddit (00:32:38)

    Navigating Reddit and Other Forums (00:34:17)

    Understanding Marketing and Content Strategies (00:35:20)

    Challenges of Early-Stage Product Development (00:38:03)

    Defining Product-Market Fit (00:44:48)

    Size of the Market (00:48:24)

    Total Reachable Market (00:49:01)

    Reaching 100% of the Paying Market (00:50:42)

    Total Addressable Market (00:51:00)

    Escape Velocity (00:54:20)

    Business Plateau (00:55:39)

    Hiring and Team Growth (00:57:24)

    Managing People (01:03:09)

    Owner and Founder Level Thinkers (01:04:35)

    Challenges of Hiring and Paying Employees (01:05:33)

    Remote Work and Cost-Effective Hiring (01:07:18)

    Working On vs. In the Business (01:10:33)

    Achieving Work-Life Balance and Financial Success (01:14:51)

    Earning Wealth and the Challenges of Autopilot Income (01:19:44)

    Investing and Selling Assets (01:20:21)

    Tax Treatment and Selling SaaS Companies (01:21:14)

    Wealth and Freedom (01:22:09)

    Finding Happiness as an Entrepreneur (01:23:04)

    Retreats and Self-Reflection (01:30:10)

    Recommendations and Conclusion (01:31:58)

    1h 33m - Apr 22, 2024
  • #333 - The Pressure of the 30s

    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 a community with fellow creators.

    Links

    Tiago's Twitter

    Try Podsqueeze


    Timestamps

    Reflecting on the Journey (00:00:05)

    Transitioning to Indie Entrepreneurship (00:01:35)

    Navigating Societal Pressures (00:04:09)

    Challenges of Social Expectations (00:07:51)

    Self-Confidence and Entrepreneurship (00:13:36)

    Wealth and Investment Strategy (00:14:56)

    Balancing Work and Social Life (00:23:40)

    Setting up a new office space (00:25:44)

    Inviting others to work in the office (00:25:44)

    Seeking feedback and engagement (00:26:41)

    27m - Apr 8, 2024
  • #332 - Money, Time and Fun - You Can Have It All!

    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, money, or impact? Inspired by folks like Casey Neistat and Tim Ferriss, I mused on the art of delegation, automating the mundane, and setting priorities to make every moment count. Join me as I explore the true cost of entrepreneurship and whether selling Podsqueeze might just be the key to finding balance.


    Links

    Tiago's Twitter

    Try Podsqueeze


    Timestamps

    The Point of Being an Entrepreneur (00:00:11)

    Influence of YouTuber Casey Neistat (00:01:33)

    Setting Challenging Goals (00:04:01)

    Delegating Tasks and Automating Processes (00:06:29)

    Balancing Work and Personal Life (00:10:41)

    Training and Delegating Responsibilities (00:13:40)

    Automating Personal Life Tasks (00:21:03)

    Challenges and Decision-Making for Podsqueeze (00:23:06)

    Re-evaluating Podsqueeze (00:24:15)

    Setting Goals and Accountability (00:25:20)

    26m - Apr 1, 2024
  • #331 - The Tool That Most Companies Use But Don't Want You To Know

    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 prices! Get ready for a very packed episode!


    Links

    Tiago's Twitter

    Try Podsqueeze


    Timestamps

    Audiobooks and Entrepreneurship (00:00:11)

    Tiago discusses his preference for audiobooks over physical books and the complexity of entrepreneurship.


    Discovering Apollo (00:02:22)

    Tiago shares his discovery of Apollo, a tool for finding and reaching out to potential clients, and its impact on his and his wife's entrepreneurial endeavors.


    Technical Issue with Website Hosting (00:12:02)

    Tiago recounts the technical issue with his website hosting service, the downtime experienced, and his decision to switch to a different hosting provider.


    Pricing Changes (00:16:49)

    Tiago explains the decision to increase the prices of Podsqueeze, the impact on customer conversion, and the strategic considerations behind the pricing changes.


    Selling the business (00:22:10)

    Discussion on selling the business, organic growth, and profitability.


    Upcoming interviews (00:23:06)

    Announcement of upcoming interviews with Dagobert and Rob Walling, and wishes for entrepreneurial success.

    24m - Mar 25, 2024
  • #330 - Top Productivity Hack Every Entrepreneur Must Know!

    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 Workweek" and the Pareto principle, and I'll share my personal tactics for managing tasks and boosting efficiency in my business.

    Links

    Tiago's Twitter

    Try Podsqueeze


    Timestamps

    Elections in Portugal (00:00:11)

    Impact of Immigration (00:02:36)

    Changes in Political Views as a Business Owner (00:05:41)

    Productivity Strategies (00:09:03)

    Automating and Delegating Tasks (00:19:54)

    Taking Time Off and Giving Responsibility (00:21:01)

    Productivity and Tim Ferriss' Book (00:21:55)

    22m - Mar 11, 2024
  • #329 - How Daniel Invests His $500K ARR Portfolio

    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 debt, which totally resonates with me as I navigate this indie maker life. We dived into his backstory, his big company sale (hello six figures!), and how he's handling his dough post-sale. Super insightful stuff on building a strong foundation before taking big leaps, and the importance of trust and due diligence when selling your biz. Plus, we got into the nitty-gritty of investing strategies and balancing risk with stability. So much to learn from this guy!


    Links

    Daniel's Twitter

    Tiago's Twitter

    Try Podsqueeze


    Timestamps

    The podcast's next phase (00:00:12)

    Selfish podcasting (00:02:02)

    Learning from interviews (00:03:32)

    Age and entrepreneurship (00:07:14)

    Starting young (00:10:39)

    Learning from failures (00:12:04)

    Thinking in simpler terms (00:16:00)

    Muscle Memory and Learning (00:19:22)

    Starting as an Indie Maker (00:20:31)

    Early Work Experience and Decision Making (00:22:34)

    Mindset and Motivation for Investing (00:27:47)

    Childhood Influences and Business Strategy (00:30:00)

    Exit Strategy and Financial Success (00:33:34)

    Acquisition Details and Financial Impact (00:37:20)

    Selling the Company (00:37:45)

    Acquisition Process (00:40:39)

    Investment Strategy (00:48:00)

    Real Estate Investment (00:50:01)

    Liquidity and Safety Nets (00:53:41)

    Taxes and Accounting (00:54:52)

    Tax Rates and Comparisons (00:57:31)

    Managing Time and Operations (01:00:26)

    Investment Strategy and Criteria (01:04:36)

    Financial Aspirations and Risk Management (01:08:26)

    Reflection and Gratitude (01:12:32)

    Closing Remarks and Future Conversations (01:12:37)

    Podcasting Industry and Long-Term Investment (01:13:16)

    Stable Results and Low Churn Investments (01:14:41)

    Risk Management and Long-Term Growth (01:15:54)

    Financial Aspirations and Comfortable Living (01:16:54)

    Investing for Comfort and Security (01:18:10)

    Prioritizing Comfort and Relationships Over Wealth (01:22:36)

    1h 26m - Mar 4, 2024
  • #328 - The Book That Every Maker Needs To Read

    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 led me to a game-changing book for my biz strategy.

    Also, I'm toying with the idea of setting up a co-working space for us indie makers. How cool would that be? Stay tuned, and let's keep making waves together!

    Book: The SaaS Playbook

    Links

    DM me on Twitter

    Support This Podcast

    Join The WBE Community

    Try PodSqueeze


    Timestamps

    Struggles with Consistency (00:00:11)

    New Commitment to Consistency (00:01:15)

    Value of Consistency in Podcasting (00:02:27)

    Starting a New Podcast (00:03:39)

    Discovering a Valuable Book (00:06:54)

    Challenges of Reducing Churn (00:11:40)

    Importance of Long-Term Thinking (00:21:02)

    Exploring the Idea of Co-Working Space (00:22:53)

    25m - Feb 26, 2024
  • #327 - Why Some Products Grow And Others Don't?

    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, like YouTube and non-English speaking segments, aiming to maintain momentum and captivate early innovators.

    Links

    Support This Podcast

    DM me on Twitter

    Join The WBE Community

    Try PodSqueeze


    The frustrating smartwatch purchase (00:00:12)

    Dealing with refunds and customer complaints (00:03:21)

    Understanding early adopters and early majority (00:07:30)

    Lessons from initial product growth (00:10:53)

    Neglecting sustainable marketing strategies (00:14:06)

    Tapping into new markets and potential strategies (00:17:04)

    20m - Feb 10, 2024
  • #326 - You Need To Grow Together With Your Business

    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


    Timestamps

    Skills required to scale a product (00:01:18)

    Understanding churn and its impact (00:03:39)

    Delegating tasks and reclaiming time (00:06:57)

    Investing in sustainable marketing strategies (00:10:07)

    Expanding touchpoints and marketing efforts (00:12:08)

    Learning from others' experiences (00:16:01)

    Conscious use of time and resources (00:19:25)

    Becoming the Best Entrepreneur (00:20:28)

    Closing Remarks (00:21:23)

    22m - Feb 2, 2024
  • #325 - Don't Waste Time... Pay For A Marketing Expert Instead!

    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 to engage different customer segments through multiple touchpoints. I'll share my experience in recognizing the power of expertise, detailing how bringing in SEO and Instagram marketing specialists took my business to new heights. Plus, I'll discuss how I broke through a growth plateau by embracing automation and delegation. And don't miss out—I'm inviting you to join my now-free community for entrepreneurs, a place where strategic investments meet exponential growth. Join me on this adventure!

    Links

    Support This Podcast

    DM me on Twitter

    Join The WBE Community

    Try PodSqueeze


    Timestamps

    Marketing as an Entrepreneur (00:00:08)

    Tiago discusses the challenges of marketing as an entrepreneur and the need to change skill sets.


    Learning as an Entrepreneur (00:02:43)

    Tiago emphasizes that entrepreneurship is a lifelong learning process and shares his journey of learning and growth.


    Investing in Passive Sources (00:04:44)

    Tiago talks about the importance of investing in passive sources of users and the impact on sustained growth.


    Strategies for Marketing (00:08:54)

    Tiago discusses the need for multiple touchpoints and strategies for automating marketing efforts.


    Utilizing Shorts for Marketing (00:12:40)

    Tiago shares the experience of using shorts for marketing and the initial success and challenges faced.


    Analyzing Conversion Rates (00:16:59)

    Tiago explains the importance of analyzing different sources of marketing and their impact on conversion rates.


    Automating tasks (00:19:03)

    Discussing the need to automate tasks to avoid burnout and focus on marketing and strategizing.


    SEO strategy (00:19:59)

    Exploring the effectiveness of hiring an expert for SEO strategy and the positive impact it had on the business.


    Utilizing expertise (00:21:57)

    Highlighting the value of hiring experts in specific fields, such as Instagram, to accelerate growth and avoid unnecessary trial and error.


    Cost-effective marketing (00:22:52)

    Evaluating the cost-effectiveness of hiring individuals for marketing strategies instead of delegating to expensive agencies.


    Community engagement (00:24:43)

    Announcing the decision to make the community space free and encouraging support for the podcast through alternative means.


    Conclusion and support (00:25:33)

    Wrapping up the episode and offering ways for listeners to support the podcast while also making the community space accessible for free.

    26m - Jan 14, 2024
  • #324 - Starting a Podcast in 24 Hours: Guerrilla Marketing 101!

    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 launch strategies, the innovative use of AI in our production, and how our podcast has skyrocketed PodSqueeze's marketing efforts. But it's not all work—I'll also get real about the challenges of maintaining work-life balance, avoiding burnout, and why personal well-being should never take a backseat. Join me as we explore the hustle and the humanity of entrepreneurship.


    Links

    DM me on Twitter

    Join The WBE Community

    Try PodSqueeze


    Timestamps


    Tiago's Decision to Focus on Marketing (00:00:09)

    Tiago discusses his decision to focus solely on marketing for the first three months of 2024 and the reasons behind it.


    The Concept of Guerrilla Marketing (00:06:43)

    Tiago explains the concept of guerrilla marketing and its importance for their marketing strategy, emphasizing the need for low-budget, high-impact campaigns.


    Creating a Podcast for PodSqueeze (00:10:27)

    Tiago and his co-founder, John, brainstorm the idea of creating a podcast for PodSqueeze, discussing the benefits and reasons behind the decision.


    Challenges and Success in Starting the Podcast (00:13:17)

    Tiago shares the challenges and success of starting the podcast in just 24 hours, including the overwhelming response from potential guests and the technical aspects involved.


    Using AI for Podcast Intros and Outros (00:18:45)

    Tiago discusses the use of AI for creating podcast intros and outros, detailing the process and the outcome of using this technology.


    Initial Success of the Podcast Launch (00:20:28)

    Tiago reflects on the initial success of the podcast launch, including the viewership and downloads within the first 24 hours, and the creation of short content for the podcast.


    The launch of "What the F is PodSqueeze" campaign (00:21:26)

    Tiago discusses the idea of a marketing campaign to create buzz and attract attention for PodSqueeze.


    Struggling to balance work and social life (00:22:42)

    Tiago reflects on the challenge of balancing work commitments with maintaining a social life and personal well-being.


    The dilemma of prioritizing work over personal life (00:23:46)

    Tiago explores the conflict between dedicating himself entirely to work and the desire to enjoy a balanced personal life.


    Realizing the importance of work-life balance (00:24:52)

    Tiago acknowledges the need to prioritize mental health and social aspects alongside work commitments.


    Striving for a work-life balance (00:25:26)

    Tiago discusses the need to change his mindset and focus on maintaining a balance between work and personal life.


    Acknowledging the importance of disconnecting from work (00:26:02)

    Tiago emphasizes the significance of disconnecting from work and engaging in activities for personal well-being.


    Seeking balance and consistency (00:27:49)

    Tiago encourages feedback and shares his struggle with maintaining consistency while striving for work-life balance.

    29m - Jan 7, 2024
  • #323 - The Crazy Journey from $0 to $100K in One Year!

    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 details of negotiations and taxes. Plus, we're getting real about the future—do we sell or keep growing? Join us as we share the lessons learned and the unbreakable bond we've built along the way.


    Links

    DM me on Twitter

    Join The WBE Community

    Try PodSqueeze


    The journey begins (00:00:11)

    Tiago and Jerome reflect on their decision to work together and the challenges they faced.


    The struggles of entrepreneurship (00:02:05)

    Jerome discusses his frustration with freelancing and skepticism about entrepreneurship.


    Creating Pod Squeeze (00:06:57)

    The co-founders brainstorm and develop the idea for Pod Squeeze, emphasizing the importance of rapid prototyping.


    Early traction and pricing strategy (00:09:31)

    The co-founders discuss the initial traction and pricing adjustments for Pod Squeeze.


    Rapid growth and product launch (00:14:17)

    The excitement and success of Pod Squeeze's rapid growth and product launch are highlighted.


    Impact on confidence and mindset (00:20:44)

    Jerome shares how the success of their business has positively impacted his confidence and mindset.


    Financial success and confidence (00:21:12)

    Discussion on financial success leading to increased confidence and the illusion of being a genius.


    Validation and confidence through business success (00:22:27)

    The validation and confidence gained from proving oneself through successful business ventures.


    Transition from freelancing to full-time business (00:27:43)

    Jerome's decision to transition from freelancing to focusing solely on the business, impacting his quality of life.


    Negotiation and decision-making (00:35:19)

    Insights into negotiation strategies and decision-making processes, including differences in approaches between the co-founders.


    Challenges of transitioning to a product company (00:39:29)

    The frustrations and challenges of transitioning to a product company, including tax issues and negotiations with partners.


    Frustration with Tax and Legal Issues (00:40:39)

    Tiago and Jerome discuss the frustration and challenges they faced with taxes and legal issues for their business.


    Concerns about Business Growth (00:43:06)

    Jerome expresses concerns about the stagnation and decline in the growth of their business, Pod Squeeze.


    Decision to Pivot or Maintain (00:46:27)

    Jerome urges Tiago to consider pivoting their business strategy due to the stalling growth of Pod Squeeze.


    Debate on Future of Pod Squeeze (00:52:55)

    Jerome and Tiago discuss the options of either selling Pod Squeeze or maintaining it as a steady stream of income, and the possibility of starting a new project.


    Reflection on the Year and Future Plans (00:54:26)

    Tiago and Jerome reflect on the challenges faced during the year and express uncertainty about their energy for building something from scratch in the future.

    56m - Dec 30, 2023
  • #322 - Startup Plateau and Conquering the Early Majority

    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 investor, where we delve into marketing strategies and the struggle to reach the early majority. As the year comes to an end, I reflect positively on my financial stability and encourage listeners to take a break during the holiday season. Stay tuned for the next episode!


    Links

    DM me on Twitter

    Join The WBE Community

    Try PodSqueeze


    Timestamps


    Tiago's Busy Schedule and Tasks (00:00:13)

    Tiago discusses his busy schedule and the tasks he needs to complete before Christmas.


    Challenges of Entrepreneurship and Stagnation (00:01:32)

    Tiago talks about the challenges of entrepreneurship and the stagnation they are experiencing with Pod Squeeze.


    Realization of Achievements and Frustration (00:02:55)

    Tiago shares his realization that their achievements with Pod Squeeze are actually impressive, despite feeling frustrated.


    The challenges of entrepreneurship and reaching a plateau (00:09:08)

    Tiago discusses the challenges of entrepreneurship and the stagnation they are experiencing with Pod Squeeze.


    Marketing strategies for early adopters and early majority (00:10:13)

    Tiago talks about the different marketing strategies needed for early adopters and early majority, and how they have reached a plateau.


    Strategies for growth and going viral (00:12:44)

    Tiago discusses the limited resources of a bootstrapped company and explores strategies for growth, including SEO, YouTube, and going viral.


    Tiago's Busy Schedule and Tasks (00:17:08)

    Tiago discusses his busy schedule and the tasks he needs to complete before Christmas.


    Challenges of Entrepreneurship and Stagnation (00:17:08)

    Tiago talks about the challenges of entrepreneurship and the stagnation they are experiencing with Pod Squeeze.


    Realization of Achievements (00:18:26)

    Tiago shares his realization that their achievements with Pod Squeeze are actually impressive, despite feeling frustrated.

    18m - Dec 22, 2023
  • #321 - How to go from $100K to $1M with My Indie Business?

    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 frustrations with the bureaucratic process in Portugal and reflect on my entrepreneurial journey. Additionally, I will reveal how my company reached a major milestone of earning over $100k and discuss our future growth plans. I will emphasize the importance of strategic thinking, automation, delegation, and long-term marketing strategies. Finally, I will invite you, the listeners, to join our private community for indie makers. Let's dive in!


    Links

    Andrew Twitter

    DM me on Twitter

    Join The WBE Community

    Try PodSqueeze


    Tiemstamps

    The Millennial Dream (00:00:11)

    Tiago talks about acquiring a home and the excitement of owning a place in the current real estate market.


    The Frustration of Buying Gifts (00:02:37)

    Tiago expresses his lack of excitement for receiving expensive gifts and his thoughts on the point of gift exchanges like Secret Santa.


    Measuring Branding and Influencer Impact (00:05:41)

    Tiago discusses the challenge of measuring the impact of branding and influencers on a company and shares his experience with tracking user acquisition sources.


    The frustration with rules and regulations (00:12:00)

    Tiago discusses the frustration with rules and regulations in Germany and Portugal, and the lack of trust in the government.


    The challenges of understanding fiscal law (00:13:10)

    Tiago talks about the frustrations of navigating fiscal law in Portugal and the lack of guidance from accountants.


    The gray area of interpreting the law (00:15:10)

    Tiago discusses the ambiguity and interpretation of laws, using the example of setting up a company in Dubai and the varying interpretations of what it means to have a connection to a country.


    Scaling from 100k to 5 million (00:23:45)

    Tiago discusses his goal of scaling his business from 100k to 5 million and his plans to automate processes and hire freelancers.


    Short-term thinking and marketing gap (00:24:43)

    Tiago reflects on the mistake of short-term thinking and not planning for the gap between cold emailing and other marketing strategies like SEO and brand marketing.


    Preventing fires and strategic thinking (00:25:45)

    Tiago emphasizes the importance of preventing fires as an entrepreneur and the need for strategic thinking, including investing in SEO and planning features ahead of time.

    29m - Dec 12, 2023
  • #320 - Interviewing Andrew Gazdecki About How To Sell a Bootstrapped Startup

    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 the right people, and understanding the buyer's perspective when selling a business.

    Plus, Andrew shares some fantastic marketing strategies and emphasizes the importance of creativity and uniqueness.

    Links

    Andrew Twitter

    DM me on Twitter

    Join The WBE Community

    Try PodSqueeze


    Timestamps

    The world of selling startups (00:01:20)

    Discussion about the nuances and misconceptions of selling startups, including the common belief of multiplying revenue by ten as the selling price.


    Branding and marketing techniques (00:02:29)

    Exploration of the importance of brand awareness and marketing techniques that may not bring immediate customers, and how to measure their effectiveness.


    Entrepreneurial background and early businesses (00:04:46)

    Andrew's upbringing in a beach town, his curiosity about wealth, and his early experiences starting businesses as a means to acquire money and the things he desired.


    Financial Literacy and Parental Money Management (00:10:40)

    Discussion on the lack of financial literacy and the challenges faced by parents in managing money.


    Possibility of Wealth for Individuals from Poor Backgrounds (00:11:54)

    Exploration of whether it is possible for anyone from a poor family to become wealthy, highlighting the importance of taking action and not making excuses.


    Mental Resilience and Problem-solving in Entrepreneurship (00:13:33)

    The impact of overcoming hardships on building mental resilience and problem-solving skills in entrepreneurship, emphasizing the ability to love and work through challenging situations.


    The shift to white labeling and distribution strategy (00:20:16)

    The speaker discusses how they partnered with an agency in Switzerland to white label their software, leading to a boom in sales and a shift in target customers.


    Transition from selling to small businesses to selling to agencies (00:21:25)

    After the partnership with the agency, the speaker's company started selling packages of mobile apps to agencies, resulting in a significant increase in sales and a shift in the sales process.


    Importance of distribution mindset and building a team (00:26:26)

    The speaker emphasizes the shift from product development to distribution mindset and the importance of building a team to handle various aspects of the business, such as marketing, sales, customer support, and product development.


    The importance of realistic entrepreneurship portrayal (00:31:06)

    Discussion on the shift in entrepreneurship coverage and the need for a more realistic view.


    Selling a goal, lifestyle, and viewpoint (00:33:05)

    Exploration of the power of selling beyond the product, using Nike as an example.


    Defining success and the role of teams (00:36:34)

    Reflection on the different paths to success and the choice to work alone or with a team.


    The topic of delegating tasks (00:41:22)

    Discusses the importance of delegating tasks that hold you back and that you dislike, in order to focus on high-impact activities within the business.


    The topic of hiring engineers (00:42:15)

    Shares a personal experience of hiring engineers through a job board and Upwork, emphasizing the importance of trust and recommendations when evaluating talent.


    The topic of valuing and selling a business (00:44:14)

    Explores the possibility of selling a business, evaluating its worth based on what someone is willing to pay and considering the buyer's perspective. Discusses the complexities of valuations, financial buyers, and the importance of running a competitive process to maximize valuation.


    The terms of selling a business (00:51:18)

    Discussion on the terms of selling a business, including the desire for a clean break, all cash on close, and quick due diligence.


    The process of selling a business (00:53:56)

    Exploration of the process of selling a business, including lowballing the initial valuation, attracting buyers, and creating urgency through a deal schedule.


    Benefits of buying bootstrap businesses (00:56:50)

    Explanation of why buyers are interested in acquiring bootstrap businesses, such as cleaner cap tables, niche products, profitability, and capital efficiency.


    Financial Buyers (01:01:35)

    Financial buyers are interested in profitable businesses with low churn and reliable recurring revenue.


    Strategic Buyers (01:01:37)

    Strategic buyers look for products that can help them enter new markets or add to their product suite for cross-selling.


    Private Equity Firms (01:02:45)

    Private equity firms, like the one mentioned, acquire startups every week and may cross-sell products or hold profitable businesses.


    Valuing a business based on profitability (01:11:53)

    Discussion on how buyers value a business based on profitability rather than revenue.


    Measuring the impact of branding (01:15:11)

    Discussion on measuring the impact of branding, including tracking Google searches and the importance of word of mouth marketing.

    1h 24m - Dec 1, 2023
  • #319 - From Cheating at a Podcast Festival to Sponsoring It

    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 Portuguese market.


    Links

    DM me on Twitter

    Join The WBE Community

    Try PodSqueeze


    Timetsamps

    Tiago's sister starts her podcast (00:01:23)

    Tiago's sister starts her own podcast during the pandemic and receives positive feedback for her comedic content.


    Tiago hacks the podcast festival website (00:04:37)

    Tiago hacks the website of a podcast festival to increase his sister's chances of winning an award.


    Pod Squeeze sponsors the podcast festival (00:06:44)

    Pod Squeeze, Tiago's company, sponsors and organizes events at the podcast festival, leading to networking opportunities and potential clients.


    Tiago's Oscars Speech (00:10:34)

    Tiago talks about his sister being nominated for a podcasting prize and giving a speech at the awards ceremony.


    Ungrateful Prize Winner (00:12:18)

    Tiago discusses the incident where the prize winner publicly stated that they didn't need the prize, causing frustration.


    Conflict with Co-Founder (00:16:06)

    Tiago explains the conflict between him and his co-founder regarding the importance of networking and measuring success.


    The overwhelmed feeling of being bootstrapped (00:19:57)

    Tiago discusses feeling overwhelmed with the various aspects of his business and the frustration of not being able to move forward due to the lack of resources.


    The growth of the indie hacker movement (00:20:50)

    Tiago talks about the positive development of the indie hacker movement, its increasing popularity among entrepreneurs, and the interview of an indie hacker on a Portuguese TV show.


    Tiago's interview on a Portuguese podcast (00:22:03)

    Tiago shares his happiness about being interviewed for a Portuguese podcast and being able to discuss his work and experiences with his family.

    24m - Nov 24, 2023
  • #318 - How Makers Take the Most Out Of a Tech Conference

    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 quiet area for meetings. I'll also open up about my struggles with social anxiety at networking events. Plus, I'll emphasize the importance of business cards and share some interesting interactions with industry professionals.


    Links

    Join The WBE Community

    Try PodSqueeze

    DM me on Twitter


    Timetsamps

    Finding Success at Web Summit (00:01:23)

    Tiago discusses his experience at the Web Summit tech conference, including controversies, ticket acquisition, and preparation tips.


    The Overwhelming Nature of Web Summit (00:02:33)

    Tiago describes the overwhelming size and structure of the Web Summit, with multiple pavilions, talks, booths, and an app for networking.


    Networking and Scheduling at Web Summit (00:06:38)

    Tiago shares his strategy for networking at the conference, including using the app to connect with people, scheduling back-to-back talks, and finding a quiet meeting area.


    Blushing and Social Anxiety (00:10:31)

    Tiago discusses his experience with blushing and social anxiety, how it affects his interactions, and the potential connection to anxiety or phobia.


    Awkward Networking Events (00:11:29)

    Tiago talks about feeling awkward during networking events, particularly when approaching people and breaking the ice.


    Interactions and Insights from Podcasters (00:12:20)

    Tiago shares his interactions with podcasters and people in the industry, discussing the struggles of podcasting, learning about Spotify's role, and offering help and advice.


    The card is an effective networking tool (00:19:31)

    Tiago discusses how he used his business card to approach someone and make a connection.


    Offering a discount on the card (00:20:18)

    Tiago explains how his business card also includes a discount and information about his product.


    The podcast has a strong and supportive community (00:21:03)

    Tiago expresses gratitude for the listeners and mentions the active community of indie makers who support the podcast.

    24m - Nov 17, 2023
  • #317 - This Was Probably My Biggest Mistake Ever

    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 importance of data-driven decisions and monitoring metrics. Plus, I'll be sharing my frustrations with high taxes and corruption in Portugal, and why I believe in advocating for change rather than relocation.


    Links

    Join The WBE Community

    Try PodSqueeze

    Buy The Bootstrapper's Guide

    DM me on Twitter


    Timetsamps

    Blocking the Upload Feature (00:02:42)

    Tiago discusses his decision to block the upload feature on Pod Squeeze to prevent fake accounts and the impact it had on reducing the number of fake accounts.


    Revenue Decline Concerns (00:07:02)

    Tiago and Joanne express their worries about the declining revenue of Pod Squeeze and discuss the possible reasons behind it.


    Increase in Empty Accounts (00:09:19)

    Tiago analyzes the increase in empty accounts on Pod Squeeze after blocking the upload feature and realizes that it may have negatively impacted conversion rates.


    The Mistake (00:10:23)

    The speaker discusses a mistake they made by not testing a feature, resulting in a decrease in conversion rates.


    The Confusion (00:12:13)

    The speaker discusses their confusion about the unexpected increase in conversion rates despite fewer people trying out their product.


    The Changes and Decisions (00:16:27)

    The speaker talks about rolling back changes, allowing one upload per free account, and the importance of plotting and monitoring metrics.


    The taxes in Portugal (00:20:28)

    Discussion about the complexity and high rates of taxes in Portugal for entrepreneurs.


    Corruption scandal in Portugal (00:21:39)

    Frustration and powerlessness regarding the corruption scandal involving the prime minister and ministers in Portugal.


    Interviews and podcast updates (00:23:50)

    Mention of an interview with Dagobert about mental health and an upcoming interview with Andrew Decky. Also, mention of Mark selling his business and his AMA episode.

    27m - Nov 10, 2023
  • #316 - Interviewing Dagobert About How to Avoid Burnout as a Founder

    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 WBE Community

    Try PodSqueeze

    Buy The Bootstrapper's Guide

    DM me on Twitter


    Timetsamps

    The challenges of becoming official (00:04:43)

    Tiago and Dagobert discuss the process of becoming an official company and the frustrations and complexities they faced with the tax system.


    The benefits of using Lemon Squeezy (00:06:57)

    Dagobert explains how using Lemon Squeezy as a merchant of record can simplify the tax burden and accounting process for online businesses.


    The complexities of the tax system (00:10:16)

    Tiago and Dagobert discuss the complicated nature of the tax system, including the different tax rates in different countries and the deductions that can be made to reduce taxes.


    The burnout and realization of goals (00:11:21)

    Tiago discusses his burnout and how he became obsessed with reaching a monthly income of $10,000, only to realize it didn't solve all his problems.


    The risks and peace of mind (00:12:09)

    Tiago talks about the peace of mind he feels with his recurring income, although there is a small chance it could go to zero.


    The collapse and symptoms of burnout (00:18:10)

    Dagobert describes the moment his body broke down due to burnout, experiencing symptoms such as racing heart, tingling sensations, and anxiety.


    The burnout realization (00:22:24)

    Speaker 2 discusses how he initially dismissed the idea of burnout but eventually realizes that it is the cause of his symptoms.


    Impact on the business and relationship (00:25:16)

    Speaker 2 explains how his burnout affected the business and caused stress for his partner, leading to the collapse of the business.


    Living in constant stress (00:27:43)

    Speaker 2 reflects on how he got used to living in constant stress and denial as an entrepreneur, leading to his burnout.


    The challenges of relying on Twitter for income (00:31:59)

    Speaker 2 discusses the stress and pressure of depending on Twitter for income and the need to go viral.


    Dealing with burnout and self-care (00:33:02)

    Speaker 2 shares their experience of burnout and the steps they took to address it, including meditation, journaling, and therapy.


    Transitioning to a job and financial stability (00:34:04)

    Speaker 2 talks about the decision to find a job for financial stability and the relief it brought to both themselves and their partner.


    The trust and autonomy in the new job (00:42:46)

    Speaker 2 talks about being given complete autonomy in their new job as a product manager and the trust placed in them by the company.


    The value of experience and skills (00:44:16)

    Speaker 1 and Speaker 2 discuss how the skills and experience gained over the years have made Speaker 2 valuable in their current role.


    Success and recognition in the startup (00:49:41)

    Speaker 2 reflects on how their past failures and experiences in building startups have been recognized and valued by the founders of the current startup they work for.


    The beginning of the entrepreneurial journey (01:00:17)

    Tiago discusses the criteria that would make him sell his business and the challenges he may face in the future.


    Lucy's current situation (01:02:06)

    Dagobert talks about how Lucy is still trying to make the business work and the financial struggles she is facing.


    Differences in moving on (01:05:46)

    Dagobert explains how he has moved on from the business while Lucy is still trying to find a way to make it work, despite the challenges she faces.


    Recognizing and Preventing Burnout (01:10:35)

    Discussion about the importance of recognizing burnout and tips for preventing it, including the recommendation of therapy.


    The Importance of Finding the Right Therapist (01:11:36)

    Speaker 2 shares his skepticism about therapy and the importance of finding a therapist who understands the body and can provide a different perspective.


    Unlocking Stuck Energy in the Body (01:17:12)

    Explanation of how therapy can help unlock stuck energy in the body, leading to more clarity and the ability to make decisions.


    The decision-making struggle (01:20:00)

    The speakers discuss the struggle of decision-making and how it can be influenced by fear and hesitation.


    The importance of therapy for founders (01:21:06)

    They discuss the benefits of having a therapist by your side as a founder, helping to provide clarity and objectivity in decision-making and potentially saving time and avoiding ego-driven decisions.


    Couples therapy for co-founders (01:23:14)

    They explore the idea of co-founder therapy and how it can help address issues and improve communication between co-founders, potentially preventing mistakes and improving the overall success of the startup.


    Regaining Power and Mental Support (01:29:30)

    Tiago compares being an entrepreneur to being an athlete and discusses the importance of mental support in achieving success.


    Learning Soft Skills and Balancing Work (01:30:50)

    Dagobert talks about learning soft skills, finding balance, and prioritizing health and enjoyment in his work.


    New Powers and Taking a Different Approach (01:33:03)

    Dagobert shares his new perspective on work, focusing on having productive and meaningful hours rather than overworking himself.

    1h 36m - Nov 4, 2023
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