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I Should Have Learned This Sooner – Discussing life lessons for self-improvement
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I Should Have Learned This Sooner – Discussing life lessons for self-improvement

Author: Tim Winfred

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We each have a different life path that leads to our success, but success looks different for everyone. In the I Should Have Learned This Sooner self-improvement podcast, host Tim Winfred dives into conversations with guests to discuss the life lessons we wish had learned sooner: From financial education, money and debt, mental health, entrepreneurship, career, starting a business, personal relationships, and more. Each episode is loaded with personal development and self-improvement tips, and probably a few bad jokes (that only the Millennial generation will get, most likely). Let’s dive into these topics together with an open mind and a desire to thrive. Follow Tim on Instagram and Twitter at @contimporary and visit LearnedSooner.com for more information.
27 Episodes
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In this episode of the "I Should Have Learned This Sooner" podcast, host Tim Winfred sits down with Rachel Ramirez, a nurse turned real estate investor, to discuss her journey into house hacking and her goal of achieving financial independence. Rachel shares how she transitioned from paying high rent to owning a property that covers her mortgage through rental income. They delve into the house hacking strategy, the challenges and rewards of being a landlord, and the mindset shift required to take the leap into real estate investing. Join Tim and Rachel as they explore the power of house hacking and how it can pave the way to financial freedom. Don't miss this insightful conversation filled with valuable tips and inspiration for anyone looking to break free from the rental cycle and build wealth through real estate.
In this episode of the "I Should Have Learned This Sooner" podcast, host Tim Winfred engages in a captivating conversation with Neal Brownell, also known as The Crazy Inventor. Neil shares his personal journey of self-discovery and growth, highlighting the profound impact of destroying limiting beliefs and embracing self-worth.From a young age, Neal was labeled as mentally deficient due to his visual impairment. However, a pivotal moment occurred when his now-retired teacher, Mrs. Anderson, saw beyond these labels and recognized Neal’s intelligence. Through her unwavering belief in him and the assignments she gave, Neal’s perception of himself began to shift.The discussion delves into the power of the brain and its ability to confuse reality with vivid imagination. Neal emphasizes that our brains cannot distinguish between past experiences and present moments, often leading to repetitive patterns of behavior unless we consciously reframe our beliefs.With vulnerability and authenticity, Neal recounts his journey of self-discovery, including the importance of therapy and coaching in fostering personal growth. The conversation touches upon the transformative potential of breaking generational curses and liberating oneself from the limitations imposed by past conditioning.Join Tim and Neal as they explore the profound impact of recognizing self-worth, challenging societal labels, and embarking on a journey of personal growth. Discover how unraveling limiting beliefs can lead to a life of authenticity, empowerment, and happiness.Learn more about Neal and follow his journey at https://www.youreamazingandillproveit.comFor transcriptions of this episode and more, visit https://learnedsooner.com.Follow Tim Winfred on Twitter and Instagram at @contimporary (it's like "contemporary" but more fun).
In this episode of the "I Should Have Learned This Sooner" podcast, host Tim Winfred dives in a deep and insightful conversation with his guest, Tom Goss, an artist and musician based in Los Angeles. As a seasoned artist with over a decade and a half of experience in the industry, Tom shares his unique insights on what truly makes people happy and the importance of embracing the present moment in creative expression.Tom reflects on his personal journey as an artist and the lessons he has learned along the way. He highlights the significance of prioritizing self-care and meeting one's own needs before seeking validation from others. The pair delve into the transformative power of art, discussing how the creative process allows artists to capture and immortalize moments in time.Join Tim and Tom in this inspiring conversation as they dive into the depths of artistic expression and the profound impact it can have on one's journey towards self-discovery and fulfillment.Follow Tom on Instagram and Twitter at @TomGossMusic, or visit tomgossmusic.com to learn more.For transcriptions of this episode and more, visit https://learnedsooner.com.Follow Tim Winfred on Twitter and Instagram at @contimporary (it's like "contemporary" but more fun).
In this episode, host Tim Winfred sits down with Mindy Jensen, host of the Bigger Pockets Money Podcast. Together, Tim and Mindy discuss their shared passion for real estate and dive into Mindy's journey as a real estate agent and house flipper.Mindy shares why she decided to pursue a career in real estate, her love of looking at houses, and what inspires her creativity as a house flipper. They also touch on the importance of being a responsible and caring real estate agent who prioritizes the needs of their clients.Join Tim and Mindy as they delve into the world of real estate. If you are interested in becoming a real estate agent, you won't want to miss this episode.Follow Mindy on Instagram and Twitter at @MindyAtBP.For transcriptions of this episode and more, visit https://learnedsooner.com.Follow Tim Winfred on Twitter and Instagram at @contimporary (it's like "contemporary" but more fun).
Join host Tim Winfred as he delves into the world of personal growth and financial advice in the tipped industry. In this episode, Tim interviews Barbara Sloan, author of the book "Tipped," which offers invaluable financial guidance for the millions of Americans working in tipped industries.Barbara shares her expertise and insights gained from her 20 years of experience as a bartender, stripper, go-go dancer, and more. Discover the challenges faced by tipped workers, the unique financial considerations they encounter, and the strategies to achieve financial freedom in this often overlooked sector.If you work in the service industry or know someone who does, this episode is a must-listen. Learn how to navigate the complexities of tipped income, overcome financial obstacles, and embrace a mindset of wealth-building. Let’s embark on a journey towards financial empowerment in the tipped industry together.Follow Barbara on Instagram and Twitter at @tippedfinance, or visit https://tippedfinance.com for more information.
 In this episode of the "I Should Have Learned Sooner" podcast, host Tim Winfred sits down with Rahkim Sabree, a financial trauma specialist, to explore the concept of financial trauma and its impact on individuals' relationship with money. Rahkim shares his definition of financial trauma and explains how it exists on a spectrum, ranging from major traumatic events like evictions and job losses to smaller traumas like receiving poor financial advice.Drawing from personal experiences of growing up in poverty and later transitioning to entrepreneurship, Rahkim discusses the profound impact of financial trauma and the motivation it can create for achieving financial success. He also delves into the challenges and mindset shifts involved in transitioning from relying solely on investments to living off those funds.Join Tim and Rahkim as they navigate the complexities of financial trauma, discuss strategies for overcoming insecurities, and emphasize the importance of financial empowerment.Connect with Rahkim and learn more about financial trauma at https://rahkimsabree.com and https://rahkimsabree.substack.com/For transcriptions of this episode and more, visit https://learnedsooner.com.Follow Tim Winfred on Twitter and Instagram at @contimporary (it's like "contemporary" but more fun)
In this week's episode, host Tim Winfred sits down with Ian Jimeno, a real estate agent and geologist, to delve into lessons of personal growth and the importance of embracing one's own path.Ian shares his own journey, from starting out as a geologist to eventually becoming a real estate agent and investor in Denver. They discuss the power of pursuing one's passions, overcoming fears of judgment, and living life unapologetically.Join Tim and Ian as they explore the idea that people's opinions should not hold us back from chasing our dreams, and that the ones who truly care about us will support us no matter what. Get ready for an inspiring conversation filled with valuable insights and practical advice on personal growth and breaking free from the shackles of societal expectations.
In this episode of "I Should Have Learned Sooner" podcast, Tim Winfred interviews Shandai Person, a senior frontend engineer at Netflix and a mother to a beautiful five-year-old boy. Shandai talks about her journey in overcoming impostor syndrome and how she used vulnerability to lead her teams at Netflix. She also shares her personal finance journey with investing in the stock market and offers advice for those who are scared about investing. Tune in to this episode to learn more about Shandai's inspiring story of personal growth and her valuable insights about investing in stocks.
In this episode of the "I Should Have Learned this Sooner" podcast, I sit down with Tracy Lee, a business owner and entrepreneur, to discuss the FIRE movement and financial freedom. Together, we explore the ideas behind Financial Independence Retire Early (FIRE), which allows people to maintain lifestyle without needing to work tirelessly to retirement.Tracy shares her personal journey towards financial freedom and how it has allowed her to get out of feeling trapped because of finances. We also discuss the misconceptions around success and how it's important to understand what truly motivates us to achieve our goals. Tune in for an inspiring conversation about achieving financial freedom and living the life you want.Connect with Tracy and learn more about her journey on Twitter at @ladyleet.For transcriptions of this episode and more, visit https://learnedsooner.com.Follow Tim Winfred on Twitter and Instagram at @contimporary (it's like "contemporary" but more fun)
In this episode of the "I Should Have Learned that Sooner" podcast, I sit down with author and People Operations Consultant, Isidora Torres, to talk the importance of reframing one's life and taking a different angle when faced with challenges.. Isidora shares her insights on rethinking work culture, employee engagement, and how the introduction of hybrid work culture impacts mental health.We also discuss the idea of living life in radical amazement, taking nothing for granted and finding amazement in everything around us. Isidora also shares her journey of evolving and changing over time, from publishing a book to pursuing a master's degree to become a therapist.The conversation also delves into the topic of affording one's lifestyle and how making a high income doesn't necessarily mean you can afford the lifestyle you desire. Isidora's personal experiences and insights provide valuable lessons for anyone looking to reframe their life and achieve personal and professional growth.Connect with Isidora and learn more about her journey on Twitter at @isidoramae and on Instagram at @isidoramaetorres.For transcriptions of this episode and more, visit https://learnedsooner.com.Follow Tim Winfred on Twitter and Instagram at @contimporary (it's like "contemporary" but more fun)
Join host Tim Winfred in this episode of the "I Should Have Learned the Sooner" podcast as he sits down with Bryan Balducki, an investor-friendly realtor with the FI Team and EXP Realty. Bryan shares his inspiring story of personal growth and financial independence, starting from his early exposure to money management through Dave Ramsay's Financial Peace University at the age of eleven, to becoming a successful real estate investor and agent in the Denver market.Bryan reflects on the valuable lesson he learned about the importance of doing what is hard instead of seeking comfort in easy choices, as he navigated through the challenges of the 1099 world and pursued his passion for real estate investing. He also shares insights on how he overcame worries and anxieties about the future by staying present and handling issues as they come along with ease.If you're looking for inspiration and practical tips on achieving financial independence, overcoming challenges, and embracing personal growth, this episode is a must-listen. Connect with Bryan and learn more about his journey on Instagram at @bryanbalducki.For transcriptions of this episode and more, visit https://learnedsooner.com.Follow Tim Winfred on Twitter and Instagram at @contimporary (it's like "contemporary" but more fun)
Growing up in a low-income family can be challenging, and it can make financial freedom seem like an unattainable goal. In this episode, Danielle Daly shares her inspiring journey of going from a $30,000 income to buying a house in just two years. Hear her valuable insights about how to overcome the barriers that life throws your way in order to achieve success.Danielle shares so many nuggets of wisdom about the importance of taking action NOW and not letting fear hold you back. She emphasizes the significance of self-reflection and how it can help you learn more about yourself.Even if you encounter failure, Danielle suggests turning those losses into a lesson and staying forward-thinking. Her story is a testament to the fact that hard work, determination, and the right mindset, can help you accomplish any goal.Follow Danielle's journey on Instagram at @daniellefdaly to stay up to date with her house hacking journey.For transcriptions of this episode and more, visit https://learnedsooner.com.Follow Tim Winfred on Twitter and Instagram at @contimporary (it's like "contemporary" but more fun)
Join me as I sit down with Tom Brickman, aka "The Frugal Gay," to hear his inspiring story of achieving financial independence. From working at a movie theater and selling products on eBay, to investing in real estate and improving the quality of rental homes, Tom has come a long way.Discover what motivated Tom to make the leap from traditional employment to self-employment; learn from his experiences and understand what it means to achieve W2 freedom.Tom shares his expertise on mortgage loan points, giving you the inside scoop on how to save money and when buying your first... or tenth... home.Connect with Tom and learn more about his journey at https://thefrugalgay.com. You can also follow him on Twitter at @thefrugalgay and Instagram at @thefrugalgay11.For transcriptions of this episode and more, visit https://learnedsooner.com.Follow Tim Winfred on Twitter and Instagram at @contimporary (it's like "contemporary" but more fun)
Prioritizing your time and optimizing your finances can be a fine art. In this episode, I chat with Tiffany Grant, aka "Money Talk With Tiff," about her journey with money and how she has optimized her life to tackle urgent and important tasks efficiently.  Tiff is a busy mother, podcaster, content creator, website designer, and real estate investor. Learn how she manages to juggle all these roles and still make time to relax.  Connect with Tiff and learn more about her at https://moneytalkwitht.com, or follow her on Twitter and Instagram at @moneytalkwitht.For transcriptions of this episode and more, visit https://learnedsooner.com.Follow Tim Winfred on Twitter and Instagram at @contimporary (it's like "contemporary" but more fun)
This week, I sit down for a conversation with my friend Billy Arriaga, in a time before the coronavirus changed our day-to-day lives, and we discuss finding inspiration in every day moments, recognizing when you're thinking negatively, and the importance of taking time to live in the now and recognize that you are enough. Follow Billy on Instagram at @the_red_dahlia and tune in to LearnedSooner.com for more episodes of the "I Should Have Learned This Sooner" podcast!
In this week's episode, I have a one-on-one chat with Jake Slane, a friend and colleague that I met while working in LGBTQ media. Jake shares stories of working alongside RuPaul, the struggles of balancing life and work as a partner at Producer Entertainment Group, and staying driven when others don't believe in what you're doing. I hope you enjoy this episode because I feel like I bonded with him as we talked. Check out ProducerEntertainment.com to learn more about Jake's business, and don't forget to visit LearnedSooner.com to listen to new episodes every Monday!
In this week's episode of the "I Should Have Learned This Sooner" podcast, I chat with Meg Chase, a Los Angeles-based videographer and all-around freelance badass, about why fear controls so many of our lives and how to overcome it. We also dive into anxiety and panic, and how to remain calm (even during a zombie apocalypse). I absolutely loved every minute of this conversation, and found myself both laughing and crying. I hope you enjoy this episode as much as I did. Listen to this episode and more at LearnedSooner.com or wherever you stream podcasts. And don't forget to follow Meg on Instagram at @videodisease! New episodes every Monday.
In this week's episode, I sit down with yoga and meditation instructor Paula Edwards to chat about several of my favorite topics: mindfulness, meditation, equanimity and manifesting what you want. Paula and I are a part of different generations, and this conversation was amazingly eye-opening because I got to see that, regardless of age, we all struggle in the same ways. Listen to this episode and more at LearnedSooner.com. New episodes every Monday.
This week's episode is extra special for me because I get to talk with my good friend Shahan Krakirian about the factors of drive and motivation for all people, regardless of social class. I really enjoyed this conversation because we both had epiphanies during this chat about who we are and why we are so driven toward success. Listen to this episode at LearnedSooner.com or wherever you stream podcasts, and follow or reach out to Shahan on Instagram at @shahahahan.
In this week's episode, I sit down with Dorothy Chung and talk about the struggles of being a creative, finding everyday inspiration and realizing that the process is just as important as the end product. Dorothy and I have regular sit down conversations about our creative processes, and I'm so glad to get to share this one with you. Listen to this episode and more at LearnedSooner.com, and follow Dorothy on Instagram and @hellositsdorothy.
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