Navigating the Product Journey with Andrew Askins

Grief & Pizza

#Tech #Business #Oki Doki Digital Inc #Technology #Design #Productivity #Systems #Workflow

51:57

On the Season 2 debut of Lost Cultures: Living Legacies , we travel to Bermuda, an Atlantic island whose history spans centuries and continents. Once uninhabited, Bermuda became a vital stop in transatlantic trade, a maritime stronghold, and a cultural crossroads shaped by African, European, Caribbean, and Native American influences. Guests Dr. Kristy Warren and Dr. Edward Harris trace its transformation from an uninhabited island to a strategic outpost shaped by shipwrecks, colonization, the transatlantic slave trade, and the rise and fall of empires. Plus, former Director of Tourism Gary Phillips shares the story of the Gombey tradition, a vibrant performance art rooted in resistance, migration, and cultural fusion. Together, they reveal how Bermuda’s layered past continues to shape its people, culture, and identity today. Learn more about your ad choices. Visit podcastchoices.com/adchoices…

about a year ago 1:08:45

MP3•Episode home

Selling a business creates unexpected emotional challenges, particularly around maintaining team culture and transparency during transition
The shift from founder to employee requires significant identity adjustment and emotional processing
Mindfulness practices and somatic therapy provide practical tools for managing entrepreneurial stress and anxiety
Successful entrepreneurship requires balancing optimistic vision with realistic anxiety management
Strong partnerships can provide essential emotional and strategic balance in business leadership
Teaching and public speaking effectiveness comes from authentic storytelling rather than technical perfection
Fear of judgment often blocks creative potential more than actual skill limitations
Building genuine community and psychological safety unlocks both team and individual growth

Creators & Guests

15 episodes

Navigating the Product Journey with Andrew Askins

Grief & Pizza

published about a year ago

MP3•Episode home

Takeaways

Selling a business creates unexpected emotional challenges, particularly around maintaining team culture and transparency during transition
The shift from founder to employee requires significant identity adjustment and emotional processing
Mindfulness practices and somatic therapy provide practical tools for managing entrepreneurial stress and anxiety
Successful entrepreneurship requires balancing optimistic vision with realistic anxiety management
Strong partnerships can provide essential emotional and strategic balance in business leadership
Teaching and public speaking effectiveness comes from authentic storytelling rather than technical perfection
Fear of judgment often blocks creative potential more than actual skill limitations
Building genuine community and psychological safety unlocks both team and individual growth

Creators & Guests

15 episodes

#Tech #Business #Oki Doki Digital Inc #Technology #Design #Productivity #Systems #Workflow

All episodes

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In this conversation, Alex Hillman shares his journey from web developer to co-founder of Indy Hall, one of the first co-working spaces in the United States, exploring how community building, meaningful relationships, and iterative learning have shaped his entrepreneurial path. Links Indy Hall 10k Independents Creators & Guests Marie Poulin - Host Benjamin Borowski - Host Alex Hillman - Guest…

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Enabling Autonomous Creatives with Jessica Abel 1:06:22

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1:06:22

Jessica Abel shares her extensive journey as a creative, starting as a cartoonist and evolving into a business coach for creatives. She discusses her experiences in the comics industry, the challenges of making a living as an artist, and the importance of teaching business fundamentals to aspiring artists. The conversation highlights the need for creatives to adapt their business models and find ways to support their artistic practices while navigating the complexities of the art market. Links Website Autonomous Creative Conference Creators & Guests Marie Poulin - Host Benjamin Borowski - Host Jessica Abel - Guest…

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Manifesting a More Beautiful Internet with Rob Hardy 1:34:59

10 weeks ago1:34:59

1:34:59

In this episode, we dive deep with Rob Hardy, a writer whose "devotional pursuit of a more beautiful internet" has led him to craft powerful manifestos that challenge the status quo. Rob shares his journey from filmmaker to manifesto writer, including the emotional roller coaster of entrepreneurship and his transformative experience writing "The Source" , an article on perfectionism that resonated deeply with Ben and Marie. Links Ungated Life Ungated Media Manifestory Takeaways Metrics and views destroy what makes the internet meaningful—connecting with our unique people Manifestos contain three elements: articulating what's wrong, envisioning what's possible, and building a bridge between them Perfectionism oscillates between shame and grandiosity, while healing happens in the uncomfortable valley between Community support systems show us our struggles aren't unique and we don't need to face them alone Sustainable businesses start from safety, not scarcity, which leads to chasing metrics and "best practices" Writing a manifesto transforms the creator by forcing confrontation with deeper values and identity Manifestos help startups clarify values, improve decisions, guide hiring, and attract aligned customers Creating from conversation rather than control allows for genuine connections and surprising insights Creators & Guests Marie Poulin - Host Benjamin Borowski - Host Rob Hardy - Guest…

Grief & Pizza

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Navigating the Product Journey with Andrew Askins 1:08:45

12 weeks ago1:08:45

1:08:45

In this episode, we're talking to founder Andrew Askins about his experience growing an agency, getting acqui-hired, and then getting fired. We talk about company culture, the unique challenges of being a founder, and what it's like to bootstrap a software business. Links AndrewAskins.com MetaMonster.ai Takeaways Selling a business creates unexpected emotional challenges, particularly around maintaining team culture and transparency during transition The shift from founder to employee requires significant identity adjustment and emotional processing Mindfulness practices and somatic therapy provide practical tools for managing entrepreneurial stress and anxiety Successful entrepreneurship requires balancing optimistic vision with realistic anxiety management Strong partnerships can provide essential emotional and strategic balance in business leadership Teaching and public speaking effectiveness comes from authentic storytelling rather than technical perfection Fear of judgment often blocks creative potential more than actual skill limitations Building genuine community and psychological safety unlocks both team and individual growth Creators & Guests Marie Poulin - Host Benjamin Borowski - Host Andrew Askins - Guest…

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Exploring the Psychology of Success with Dr. Corey Wilks 1:17:56

16 weeks ago1:17:56

1:17:56

In this episode, we chat with Dr. Corey Wilks, a licensed clinical psychologist and executive coach who helps high performing entrepreneurs overcome their limiting beliefs and build a values aligned life and business. We also talk about what it means to navigate entrepreneurship when you're neurodivergent. Links CoreyWilksPsyD.com Creator Alchemy Takeaways ADHD can lead to both challenges and strengths in entrepreneurship, often driving hyper-focus and creativity. Theory crafting can be a form of self-sabotage, preventing action and real-world execution. Authenticity in coaching relationships fosters trust and allows clients to embrace their true selves. Productivity should serve personal goals, not become an end in itself. Many entrepreneurs feel trapped by their own success, creating a 'gilded cage' instead of freedom. Fear of failure, ridicule, and uncertainty are common barriers for entrepreneurs. Coaching high-performing clients can be more rewarding than working with those who lack motivation. Understanding what one truly wants is crucial for personal and professional alignment. The journey of self-discovery is often complex and requires confronting uncomfortable truths. Change can be overwhelming, but it's essential for growth. Many people wait for permission to pursue their desires. Fear of success often stems from the fear of isolation. Coaching should focus on facilitating transformation, not giving advice. Fun and passion are key to successful content creation. Authenticity resonates with people and builds connections. Creators & Guests Marie Poulin - Host Benjamin Borowski - Host Corey Wilks, Psy.D. - Guest…

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Building Experiences with Joel Hooks 1:16:04

27 weeks ago1:16:04

1:16:04

In this episode we spoke with one of our favorite makers Joel Hooks on the challenges of course creation, platform development, and AI. We also explore software development, music creation, and social media while Joel shares his fitness journey and its impact on his life and work. Links Badass Courses CourseBuilder Egghead.io @joelhooks.com on Bluesky _noise_complaint on Tiktok Takeaways The importance of owning one's platform for course creation and delivery Challenges and considerations in building and maintaining course platforms The impact of platform limitations on course delivery and content creation The use of AI in content creation and its potential impact on course development The significance of tool choice for course creation and delivery The importance of prioritizing the local work environment in software development The impact of personal preferences and opinions on file format and software development The significance of data portability and interoperability in building software tools The joy and creativity involved in music production and exploration The evolving landscape of social media platforms and the role of community engagement in programming and creative endeavors The decision to prioritize fitness involves a significant mindset shift and commitment. Hiring a coach and committing to a fitness routine can lead to unexpected enjoyment in fitness activities. The evolving landscape of online platforms presents challenges and opportunities for content creators. Creators & Guests Marie Poulin - Host Benjamin Borowski - Host Joel Hooks - Guest…

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Making Things Happen with Monica Lim 1:24:43

1 year ago1:24:43

1:24:43

In this episode, we spoke with fellow Notion pro, educator, and project management expert Monica Lim about productivity and life including strategies on handling and recognizing burnout. Check out this episode if, like Monica, you love learning and making things happen! Links MonicaLim.co @MonicaLim on Twxtter Takeaways Volunteering in high-pressure situations, such as firefighting, can help build resilience and reduce nervousness in other areas of life. Teaching experience can provide valuable skills for public speaking, as it involves helping others understand and learn. Managing ADHD requires finding strategies for prioritization and focusing on important tasks. Developing principles for decision making can help in prioritizing and avoiding distractions. Helping others can be fulfilling, but it's important to set boundaries and prioritize personal well-being. Burnout is a state of emotional, physical, and mental exhaustion caused by excessive or prolonged stress. Recognizing the signs of burnout and implementing strategies for recovery is crucial in managing and preventing burnout. Creating ideal days and rituals can help maintain balance and prevent burnout. AI can be a valuable tool in offsetting burnout, particularly in research and decision-making. Curiosity can lead to a deeper understanding of AI and automation. Automation can make tasks feel like magic and increase productivity. Learning to code can provide more control and power in automating processes. It is important to identify areas that can be automated and find the entry point to automation. Prioritizing learning and having a specific goal or project in mind can help determine the value of learning to code. Creators & Guests Marie Poulin - Host Benjamin Borowski - Host Monica Lim - Guest…

Grief & Pizza

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Leveraging Curiosity with Thomas Frank 1:12:09

1 year ago1:12:09

1:12:09

Thomas Frank has been leveraging his learning through multiple businesses and media channels. Today he joins the Oki Doki team to talk about Notion, life, and his new knowledge capture tool, Flylighter. Links Flylighter Thomas Frank on YouTube Thomas Frank Explains on YouTube Learn Notion with Thomas Takeaways Transitioning from content creation to software development can be challenging, and it's important to recognize your strengths and delegate tasks that are not in your wheelhouse. Building a team and finding the right people to work with is crucial for the success of a business. When pricing a software product, it's important to consider the value it provides to users and gather feedback to determine the optimal pricing model. The future of software development lies in modular and flexible tools that can adapt to users' needs and integrate with various platforms. Structured play is an effective way to learn and explore new topics, allowing for experimentation and discovery. Breaking the habit of checking the phone first thing in the morning can lead to a more productive start to the day. Living without smartphones for a significant part of one's life can provide perspective on the need for constant connectivity. Changing focus and obsessions can lead to new creative outlets and a shift in mindset. Being closer to family and having a sense of community can be important factors in making decisions about where to live. Creators & Guests Marie Poulin - Host Benjamin Borowski - Host Thomas Frank - Guest…

Grief & Pizza

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Embracing the Creator-Founder Role with Mariah Coz 1:08:58

1 year ago1:08:58

1:08:58

In this episode, Mariah shared her unique approaches to content creation, exploring the ease and effectiveness of podcasting as a marketing channel. She reflects on her business pivots and the transition to a new business structure that allows for more spaciousness and personal growth, discussing her transition from a CEO role to a Creator-Founder role. She also shares her desire to experiment and try new things, which led her to downsize her team and focus on her own creativity. So much amazing learning in one episode; what a treat! Links MariahCoz.com Chapters (00:00) - Mariah Interview (00:13) - Building a neurodivergent friendly business (02:25) - How do you know when you're in a good or bad creative cycle? (04:31) - How do you evaluate where a project or idea might fit in your business? (12:34) - How Mariah made a podcast be an easy lift (17:48) - How did Mariah land on podcasting as her main platform? (21:43) - What is the structure of Mariah's current business? (36:10) - How did you learn that you wanted to be a creator and not a CEO? (46:31) - Being a destroyer and not always a creator (50:55) - What does your current iteration look like? (54:29) - Why would you intentionally avoiding big opportunities? (01:05:56) - Do you use any AI tools in your work currently? (01:07:07) - What's the best way for people to find out more about Mariah Coz? Takeaways Creating a neurodivergent-friendly business involves designing processes and systems that accommodate individual needs and mental health challenges. Focusing on substance over aesthetics in content creation can lead to faster and more efficient production. Podcasting can be an easy and effective marketing channel, providing a platform for sharing ideas and connecting with an audience. Transitioning from ads to podcasting can offer more freedom and flexibility in content creation and delivery. Reevaluating roles and creating spaciousness in business can lead to personal growth and a more sustainable approach to work. Transitioning from a CEO role to a creator role requires making changes to the way programs are delivered and the structure of the business. Embracing change and experimentation is essential for personal and professional growth. There is a difference between a "Creator" founder and a CEO, and it's important to understand one's own strengths and desires. The creator CEO role requires elasticity and the ability to transition between different roles and responsibilities. Fear of visibility can hold back growth, but saying yes to new opportunities can lead to personal and professional development. Creators & Guests Marie Poulin - Host Benjamin Borowski - Host Mariah Coz - Guest…

Grief & Pizza

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Livin' the Llama Life with Marie Ng 1:11:53

1 year ago1:11:53

1:11:53

Marie Ng, founder of Llama Life, shares her journey from advertising to software development and the challenges and successes she encountered along the way. She discusses the importance of building a customer base and the resonance of her product with the ADHD community. Links LlamaLife.co Marie on Twitter Chapters (00:00) - Living the Llama Life with Marie Ng (00:28) - What has your journey been thus far? (04:50) - How long did it take to get to the first sale to another person? (10:57) - The perfect storm of COVID and everyone suddenly working from home (15:43) - The benefits of being funded vs bootstrapped (26:29) - What did you hire for when you got funded? (33:57) - Life as a founder with ADHD (01:05:18) - What are you excited about? What's coming up next? (01:08:35) - Why Llama? Takeaways Transitioning from one career to another requires dedication and a willingness to learn new skills. Building a customer base requires effective marketing strategies and resonating with a specific target audience. Seeking funding can provide opportunities for growth and expansion. Hiring the right team members is crucial for filling skill gaps and supporting the growth of the business. Hiring is a challenging and time-consuming process, but having prior experience working with someone can help ensure a good fit. Design and branding play a crucial role in creating a distinct and enjoyable user experience. Creating a supportive team environment with open communication and low ego is essential for managing ADHD as a founder. Entrepreneurship allows for more control over one's work environment and the ability to solve personal problems. Building and scaling a product involves making decisions and managing tech debt, but it's important to prioritize and focus on the customer experience. Creators & Guests Marie Poulin - Host Benjamin Borowski - Host Marie Ng - Guest…

Grief & Pizza

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Examining Post-Achievement with Khe Hy 59:19

1 year ago59:19

59:19

In this episode, we talked to Khe Hy, discussing his identity journey and transition to a post-achievement career. We explored the evolution of his interests and the challenges of defying audience expectations. Khe offered insights on success, creative expression, and time management, delving into post-achievement, and noting that financial success doesn't guarantee deep satisfaction. Links RadReads Examined Life Podcast Khe on Twitter Chapters (00:00) - Introduction (01:08) - Exploring Identity (04:17) - Seasons of Entrepreneurship (15:35) - Post-achieving Professionals (21:53) - Grieving and Letting Go of Identities (28:58) - Investing in Relationships (32:19) - Therapy Experience (37:39) - Integration and Reflection (43:28) - Practicing Rejection (50:24) - One Punch Man and Stakes Takeaways Transitioning identities is a natural part of personal and professional growth. Post-achievement professionals question the traditional playbook of achievement and seek deeper satisfaction and contentment. Success should be defined by personal values and principles, not just financial achievements. Grieving and letting go of identities is an important process in personal growth and finding fulfillment. Investing in relationships and seeking therapy can lead to personal growth and a deeper understanding of oneself and others. Psychedelic therapy can provide profound insights and experiences that can positively impact relationships and personal development. Integration and reflection are important after therapy experiences to fully process and apply the insights gained. Changing one's relationship with stakes and embracing challenges can lead to personal growth and a healthier perspective on success. Creators & Guests Marie Poulin - Host Benjamin Borowski - Host Khe Hy - Guest…

Grief & Pizza

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Nervous System Mastery with Jonny Miller 48:12

1 year ago48:12

48:12

In this episode, we spoke with Jonny Miller, the mind behind Nervous System Mastery , about the critical role of understanding our nervous system. Jonny shared insights from his personal journey through grief, leading him to delve into the connections between emotions, physicality, breathwork, and the nervous system. He introduced the concept of interoception and its importance in building emotional resilience, alongside the complexities involved in teaching and sharing the nuances of mastering our nervous systems. Our conversation also ventured into the realms of psychedelics and their potential to deepen our connection with our nervous systems, the impact of COVID-19 on professional life, and the hurdles faced while scaling an online course. Jonny's story is a testament to the power of curiosity, the expression of emotions, and the search for joy in times of sorrow. Links Nervous System Mastery Curious Humans Podcast Jonny on Twitter Chapters (00:00) - Nervous System Mastery with Jonny Miller (02:47) - The Impact of Grief (06:26) - Resources for Approaching Grief (08:15) - On Burnout (13:18) - Integration of Grief and Nervous System Work (16:15) - Transition to Teaching Nervous System Mastery (19:03) - Framing the Work (21:27) - Cultivating Interoception (24:14) - Measuring Interoception (26:29) - Exploring Psychadelics and the Nervous System (40:00) - Behind the Scenes (42:50) - Current Challenges (47:19) - Finding Jonny Takeaways Understanding and mastering the nervous system is essential for emotional resilience and overall well-being. Grief and burnout can be transformative experiences that lead to personal growth and a deeper understanding of oneself. Interoception, the ability to notice and interpret bodily sensations, is a key aspect of emotional awareness and regulation. Communicating the concepts and practices of nervous system mastery can be challenging, but finding relatable language and using personal experiences can help make it more accessible. Interoception is gaining more attention in the research community, with studies showing its correlation with conditions like ADHD and PTSD. Measuring interoception can be done through assessments like the MAIA, which evaluates different areas of interoceptive capacity. Psychedelics, like MDMA and ayahuasca, can play a role in nervous system healing by surfacing incomplete reflexes and providing a space for emotional completion. Teaching and guiding others in emotional exploration requires setting boundaries and referring individuals to somatic therapists when necessary. Grief can be a transformative experience that leads to a deeper understanding of joy and connection. Future plans include in-person retreats and strategic collaborations with freelancers or contractors. Challenges include prioritizing projects, investing in assets that appreciate over time, and maintaining a sustainable and enjoyable approach to teaching and scaling the course. Creators & Guests Marie Poulin - Host Benjamin Borowski - Host Jonny Miller - Guest…

Grief & Pizza

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Becoming Unkillable with Sara Campbell 57:49

1 year ago57:49

57:49

In this conversation, Sara Campbell discusses her work as a coach and her mission to help people develop a strong relationship with themselves. She shares her journey of becoming who she is meant to be and the importance of removing layers of who we are not. Sara also talks about the lessons she has learned from Zen Buddhism, emphasizes the value of living out loud and sharing vulnerability, as well as the importance of self-compassion and overcoming self-criticism. Links SaraCampbell.co Tiny Revolutions Sara on Twitter Chapters (00:00) - Becoming Unkillable with Sara Campbell (02:11) - Helping People Become Who They Are (04:21) - What Drew you to Zen Buddhism? (06:56) - The Specificity of Ambitions and the Doing (12:27) - Formalizing the Coaching Practice (15:16) - The Bodhisattva Vow (17:22) - Living Out Loud and Sharing Vulnerability (20:49) - Crash and Burn Moments (26:23) - Helping Others and Becoming Who You Are (29:02) - Managing Energy (34:36) - Getting Started with Meditation (38:42) - Setting Intentions and Goals (44:16) - Embracing Emergence and Experimentation (46:34) - Bringing Ideas to Light Through Podcasting (52:37) - Trojan Houses for Development (55:13) - Integrating Podcasting into Courses and Coaching (57:11) - Follow Sara Takeaways Developing a strong relationship with oneself is essential for personal growth and fulfillment. Becoming who you are means removing layers of who you are not. Zen Buddhism and the Bodhisattva vow teach the importance of mindfulness, self-acceptance, and treating oneself and others with respect and care. Living out loud and sharing vulnerability can create connections and help others feel less alone. Practicing self-compassion and overcoming self-criticism are crucial for personal well-being. Getting started with meditation can be done through apps like Headspace, Calm, and Waking Up. Start a meditation practice by using meditation apps or attending local meditation centers. Take action and start somewhere, even if it's small, to avoid getting overwhelmed by choices. Simplify belongings and focus on actions rather than material possessions. Set intentions and goals to guide your actions and progress. Experiment and embrace emergence in your personal and professional development. Consider podcasting as a medium to share ideas and engage with listeners. Integrate podcasting into courses and coaching programs to enhance the learning experience. Creators & Guests Marie Poulin - Host Benjamin Borowski - Host Sara Campbell - Guest…

Grief & Pizza

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Creating a Beautiful Future with Barrett Brooks 1:12:15

1 year ago1:12:15

1:12:15

Barrett Brooks , former COO of ConvertKit and now an executive coach, shared his deep connection with nature and the significance of confronting past pain. He reflected on the complexities and rewards of executive coaching, the balance between coaching and personal creative work, and the necessity of personal growth and clear professional agreements. Barrett discussed his own experience of leaving a company, highlighting the lessons learned about boundaries, contracts, and the challenges posed by conflicting desires for company growth. He stressed the importance of navigating company departures, processing grief, and understanding the interplay between grief and joy. Additionally, he talked about his future plans, including writing a memoir and starting a podcast. Links BarrettBrooks.com BarrettABrooks on Twitter References Richard Schwatz - No Bad Parts Reboot Coaching Emotion Sensation Wheel Francis Weller - Wild Edge of Sorrow Ruthie Ackerman Maggie Smith - You Could Make This Place Beautiful Chapters (00:00) - Introduction (06:17) - The brokenness of the natural world and organizations (12:22) - Finding inner and outer alignment (16:05) - Patterns from childhood and their influence (26:14) - Transitioning to coaching (29:50) - Coaching's influence on writing (33:13) - How would you coach yourself? (35:53) - Navigating joining and leaving ConvertKit (46:24) - The cost of joy is grief (59:34) - Power of memoirs (01:07:13) - A beautiful future Takeaways Nature can have a profound impact on our well-being and should be protected. Acknowledging and integrating past pain is essential for personal growth and success. Coaching can be a valuable tool for individuals to navigate their personal and professional challenges. Creating space for personal growth and creative pursuits is crucial for maintaining balance and fulfillment. Having clear boundaries and a contract is essential when entering into agreements. Incompatible desires for company growth can lead to conflict and ultimately the decision to part ways. Navigating the complexity of leaving a company requires open communication and a willingness to process emotions. Grief and joy are interconnected, and allowing oneself to fully experience grief can lead to a deeper appreciation of joy. Writing and ritual can be powerful tools for processing grief and creating closure. Storytelling and making meaning are important for personal growth and understanding. Creating a beautiful future involves healing and integrating past pain. Writing a memoir and starting a podcast can be powerful ways to share personal experiences and inspire others. Creators & Guests Marie Poulin - Host Benjamin Borowski - Host Barrett Brooks - Guest…

Grief & Pizza

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Making Great Decisions with Joe Hudson 56:33

1 year ago56:33