how?

how? is your go-to place to answer the question. You’ve heard ”who,” ”what,” and even ”why,” but rarely ”how.” We’re committed to identifying successful business leaders from all walks of life and giving them a platform to tell real business stories that will teach you something.

Episodes

Mar 24, 2025

24 min

In this episode, Kasey Devine interviews Summer Song, founder of Omi Live, a life shopping platform for eco-friendly brands. Summer shares her journey as an introverted entrepreneur, the challenges she faced stepping out of her comfort zone, and her vision for helping other businesses grow. The conversation delves into the innovative concept of live shopping, its potential in the U.S. market, and the importance of community building for brand success. Summer also discusses the unique challenges female founders encounter in securing funding and gaining respect in the business world.
Takeaways
Summer emphasizes the importance of stepping out of comfort zones for personal and professional growth.
Building a network and community is crucial for entrepreneurs, especially those starting from scratch.
Live shopping combines entertainment with e-commerce, creating a unique shopping experience.
Summer's vision includes helping over 100 brands grow through her platform in the next five years.
The importance of focusing on existing resources rather than overthinking what is lacking.
Female founders often face unique challenges in gaining respect and funding in a male-dominated industry.
Community building requires more than just marketing; it involves creating genuine connections.
Summer's journey reflects the blend of comfort and discomfort in entrepreneurship.
The need for continuous learning and adaptation in the ever-evolving business landscape.
Engagement with eco-friendly brands is a priority for Omi Live, inviting collaboration and feedback.
Keywords: entrepreneurship, comfort zone, live shopping, eco-friendly brands, female founders, business growth, community building, marketing strategies, self-development, networking
 
Chapters
00:00 Introduction to Summer Song and Omilife
01:56 Stepping Out of Comfort Zones
05:49 The Birth of Omilife and Live Shopping
09:35 Understanding Live Shopping
11:17 Vision for the Future
13:02 Upcoming Projects and Challenges
16:38 Introspection and Advice to Younger Self
19:44 How to Follow Summer's Journey
20:28 How Listeners Can Help

Mar 24, 2025

24 min

Mar 21, 2025

36 min

In this episode, Andrea Zechmann, Founder and CEO of Levelrie, shares her entrepreneurial journey, emphasizing the importance of personal finance, creativity, and understanding the market. She discusses the challenges of starting a company, the significance of being resourceful, and her vision for revolutionizing women's fashion by creating an end-to-end experience similar to Spotify. Andrea encourages aspiring entrepreneurs to embrace their journey and invest in themselves.
 
Takeaways:
The start of an entrepreneur's journey is often the hardest part.
Understanding personal finance is crucial for founders.
Being a good steward of money is essential for success.
Passion for your idea is key to long-term commitment.
Entrepreneurship is a superpower that everyone can harness.
Investing in yourself is the best investment you can make.
Creativity is vital in finding unique solutions as a founder.
Building connections is more valuable than climbing the corporate ladder.
The fashion industry is ripe for disruption and innovation.
Women often face unique challenges in fashion that need addressing.
Sound Bites
"You have to be a good steward of money."
"I think entrepreneurship is a superpower."
"I want to create the machine, not be a cog."
Keywords: entrepreneurship, startup, personal finance, women's fashion, business journey, innovation, creativity, leadership, founder mindset, e-commerce
Chapters
00:00 Introduction to Entrepreneurship
02:29 The Journey to Starting a Company
10:06Financial Foundations for Founders
12:39 Building the MVP and Customer Discovery
22:44 Vision for the Future of Fashion
28:27 The Superpower of Entrepreneurship

Mar 21, 2025

36 min

Mar 5, 2025

34 min

In this conversation, Katie Shahan, a founder and entrepreneur, shares her journey from working in a small business to starting her own startup, Yarlow. Katie discusses the importance of networking, building confidence, and the challenges of entrepreneurship, especially for women in tech. Katie emphasizes the need for genuine connections and support systems, exemplified by her initiative, EmpowerHer, which fosters a community for female entrepreneurs. The conversation also delves into the innovative features of Yarlow, an app designed to help homeowners manage their properties effectively, and Katie's vision for its future.
 
Takeaways:
-Building a startup requires talking to customers, not just building in isolation.-Networking is crucial for building confidence and support in entrepreneurship.-EmpowerHer is a community for women entrepreneurs to connect and support each other.-Finding five reliable people in your network can significantly impact your entrepreneurial journey.-Yarlow aims to provide homeowners with essential maintenance tips and resources.-Transparency in business can lead to better customer relationships and feedback.-It's important to balance creativity with market needs in product development.-Engaging with your community can lead to unexpected opportunities and connections.-The app Yarlow is designed to help homeowners manage their properties effectively.-Entrepreneurship can be a lonely journey, but building a supportive network can alleviate that loneliness.
Chapters
00:00 Introduction to Katie Shahan01:22 Building a Startup: Lessons from the Garage07:14 The Importance of Networking11:01 EmpowerHer: Creating a Supportive Community17:22 Yarlow: The Homeowner's Companion23:15 The Journey of Entrepreneurship27:40 Advice for Aspiring Entrepreneurs
 

Mar 5, 2025

34 min

Feb 17, 2025

36 min

In this conversation, Kasey Devine interviews Sabrina Rucker, CEO and Co-Founder of Storyforge, a writing platform aimed at underrepresented new writers. Sabrina shares insights into the unique work culture at Storyforge, emphasizing authenticity, creativity, and support. She discusses the challenges of traditional publishing and the mission of Storyforge to provide a clear path for aspiring writers. The conversation highlights the importance of community, mental health, and the transformative power of storytelling.
 
Takeaways:
Sabrina Rucker is the CEO and co-founder of Storyforge.
Storyforge aims to support underrepresented new writers.
The work culture at Storyforge is intentionally non-corporate and creative.
Authenticity in the workplace fosters better ideas and collaboration.
Sabrina emphasizes the importance of mental health days for employees.
Storyforge provides a clear progress bar for writers to track their publishing journey.
The platform is designed to be inclusive and accessible for all writers.
Sabrina believes that culture is more important than strategy in a company.
Community engagement is crucial for the success of Storyforge.
Storyforge aims to revolutionize the traditional publishing process.
Sound Bites
"We have a crazy work culture."
"Culture eats strategy for breakfast."
"There's gotta be a better way."
"I would love to read them."
"I would love to see what you could do."
Keywords: Storyforge, workplace culture, creativity, publishing, underrepresented writers, authenticity, startup culture, community, mental health, storytelling
Chapters
00:00 Introduction to Storyforge and Sabrina Rucker
02:32 Creating a Unique Work Culture
10:32 The Importance of Authenticity in Workplace Culture
21:31 The Vision and Mission of Storyforge
27:10 The Impact of Storytelling and Creativity

Feb 17, 2025

36 min

Feb 11, 2025

45 min

In this episode, Kasey Devine interviews Clare Richards, CEO and Co-Founder of Impacks, a company dedicated to providing parents with an easy way to purchase school supplies online. Clare shares her journey from community service to entrepreneurship, emphasizing the importance of building relationships and making meaningful asks. The conversation explores the mission of Impacks, the challenges of starting a business during the pandemic, and the role of community service in leadership development.
 
Takeaways
Community service can lead to unexpected opportunities.
Building authentic relationships is crucial for success.
Starting a business requires resilience and adaptability.
Networking should be proactive, not reactive.
The school supply market is ripe for innovation.
Impacks aims to alleviate the burden of school supply shopping for parents.
Engaging parents in giving can create a larger impact.
Community service can develop leadership skills in employees.
It's important to ask for help when needed.
A for-profit model can effectively address social issues.
Keywords: community service, entrepreneurship, school supplies, business leadership, social impact, networking, education, startup journey, nonprofit, leadership development
 
Sound Bites
"Everything happens for a reason."
"You have to invest in those relationships."
"It's much easier for me to give."
"It's a really amazing structure."
"This is a pretty good market to be in."
"It's a win-win."
"We need to earn their trust."
"We can help make it a lot better."
Chapters:
00:00 Introduction to Clare Richards and Impacts
02:05 The Role of Community Service in Business
11:49 The Journey of Starting Impacks
19:12 Building Relationships and Making Asks
28:00 Understanding Impacts' Mission and Services
32:44 The Importance of Community Service in Leadership

Feb 11, 2025

45 min

Feb 4, 2025

37 min

In this conversation, Marin Nelson shares her journey of sobriety and how it led her to co-found Sobrynth, a company focused on providing support for substance use disorder in the workplace. Marin discusses the importance of sharing personal stories, building community, and creating safe spaces for individuals to seek help. She reflects on her experiences in recovery, the challenges of starting a business, and the need for change in workplace culture regarding substance use. The conversation emphasizes the power of vulnerability and the impact of community support in recovery.
 
Takeaways:
Marin Nelson is a long-term recovery advocate and CEO of Sobrynth.
The power of sharing personal stories can foster community and support.
Creating a sober community in the workplace is essential for recovery.
Sobriety can enhance leadership and employee performance.
There is a significant gap in workplace support for substance use disorder.
Community and connection are antidotes to loneliness and substance use.
Grief can catalyze personal and professional transformation.
Entrepreneurship requires courage and a willingness to take risks.
Businesses can positively impact society while being for-profit.
It's important to trust the process and seek help when needed.
Keywords: sobriety, recovery, workplace support, substance use disorder, storytelling, community, entrepreneurship, mental health, Sobrynth, personal growth
 
Sound Bites:
"I couldn't stay silent."
"My sobriety makes me a better leader."
"If not me, who? If not now, when?"
"We need to show that businesses can do good."
"I need to talk to someone who understands."
"You're not alone. There is hope."
"You're not alone. There are 21 million of us in recovery."
Chapters:
00:00 Introduction to Marin Nelson and Sobriety Journey
02:31 The Power of Sharing Stories
04:03 From Personal Struggles to Professional Impact
06:51 Creating a Sober Community at Work
12:49 The Importance of Community in Recovery
16:39 The Catalyst for Change: Grief and Purpose
20:56 Taking the Leap: From Employee to Entrepreneur
22:50 Sobrynth: Bridging the Gap in Workplace Support
29:16 Understanding Sobrynth's Mission and Services
33:24 Advice to My Younger Self
34:54 Engaging with Sobrynth and Community Support

Feb 4, 2025

37 min

Jan 21, 2025

36 min

Summary: Ryan Shapiro, Founder of PEOMG, discusses the importance of PEOs in supporting small to medium-sized businesses. He shares his journey into the PEO industry, the complexities of finding the right PEO for businesses, and the current climate for small businesses. Ryan emphasizes the need for authenticity and responsibility in the PEO consulting space and offers insights for aspiring entrepreneurs. He also outlines the plans for PEOMG and the impact they aim to have on the industry.
 
Takeaways
Helping small to medium-sized businesses is our core mission.
Complex problems are what drive my passion.
PEOs can support a wide range of industries.
Navigating the PEO landscape requires careful evaluation.
The current business climate is challenging but full of opportunities.
Finding the right PEO is crucial for business success.
Authenticity and responsibility are key in consulting.
Entrepreneurs should assess their weaknesses.
PEOmg aims to expand and support more businesses.
Education and fun are essential in the PEO industry.
Keywords: PEO, HR outsourcing, small business, entrepreneurship, talent retention, business growth, employee support, PEO industry, consulting, business solutions, PEOMG, Ryan Shapiro
 
Sound Bites
"I like complex problems."
"It's a relationship, it's a partnership."
"Businesses are people."
"What am I really not good at?"
"We couldn't be happier about the results."
"There's nothing sexy about the PEO industry."
"We do it to educate and have fun."
Chapters: 
00:00 Introduction to PEOMG and Ryan Shapiro
02:38 The Mission Behind PEOMG
05:32 The Complexity of PEOs and Small Business Solutions
12:00 Navigating the PEO Landscape
19:49 Current Climate for Small Businesses
22:28 Identifying the Right Fit for PEOs
25:49 Advice for Aspiring Entrepreneurs
28:21 Future Plans for PEOMG

Jan 21, 2025

36 min

Jan 13, 2025

44 min

In this conversation, Kasey Devine and Christian Durfee explore the significance of community building and authentic connections in business. They discuss the journey of entrepreneurship, the importance of mindset and perspective in networking, and how curiosity can enhance relationships. Christian shares his experiences as a serial entrepreneur and the lessons learned from his ventures, including the creation of InvestLink Social, a platform designed to connect founders and investors. The discussion emphasizes the cyclical nature of business, the value of genuine interactions, the power of networking to foster growth and opportunities, and maybe even aliens.
 
Takeaways:
Business is fundamentally about human connections.
Authenticity in networking leads to meaningful relationships.
Curiosity can open doors to new opportunities.
Every entrepreneur has a unique story shaped by connections.
Imposter syndrome can be overcome by recognizing shared experiences.
Networking should be about giving rather than taking.
Building a community requires intentional effort and authenticity.
Failures are essential for learning and growth in entrepreneurship.
The journey of entrepreneurship is cyclical with ups and downs.
Your network can significantly impact your success.
 
Keywords: community building, networking, entrepreneurship, authentic connections, mindset, curiosity, startup, relationships, fundraising, investing, InvestLink Social, Christian Durfee, founder, VC, Midwest, Minnesota, Duluth
 
Chapters
00:00 Introduction to Community Building
05:58 The Journey of a Serial Entrepreneur
12:08 Mindset and Perspective in Networking
18:53 Curiosity as a Networking Tool
25:45 Building a Startup Around Connections
36:07 Lessons Learned from Entrepreneurship

Jan 13, 2025

44 min

Jan 10, 2025

38 min

In this episode, Kasey Devine interviews Adam Choe, who shares his diverse career journey from healthcare to startups and venture capital. Adam emphasizes the importance of networking, building authentic relationships, and helping others in professional growth. He discusses strategies for effective networking and the significance of creating meaningful connections. Adam also reflects on his goals for 2025, focusing on impactful work in healthcare and AI.
 
Takeaways:
Networking is crucial for career transitions.
Opportunities often arise from connections made through networking.
Start networking early in your career.
Most people are willing to help if approached genuinely.
Building authentic relationships can lead to unexpected opportunities.
Helping others can create a positive ripple effect in your network.
Networking should be treated as a part-time job.
It's important to stand out when reaching out for opportunities.
Meaningful connections can lead to professional growth.
Your network can significantly impact your career trajectory.
Keywords: career transitions, networking, professional growth, mentorship, healthcare, AI, startups, personal development, relationships, connections
 
Sound Bites
"I feel stuck in a certain lane."
"You need to stand out."
"Your network is your net worth."
Chapters
00:00 Introduction to Adam Choe's Journey
10:31 The Power of Networking
19:54 Building Authentic Connections
27:37 The Importance of Helping Others
32:32 Looking Ahead to 2025

Jan 10, 2025

38 min

Jan 7, 2025

32 min

In this conversation, Rachel Frosch, founder of Mom Badge, shares her journey of building a startup aimed at supporting and celebrating mothers. She discusses the importance of community, the technology behind her digital gift card marketplace, and the psychological aspects of risk and hope in entrepreneurship. Rachel emphasizes the need for connection and support among mothers and encourages others to engage with her mission.
 
Takeaways:
Building a startup is a significant risk but also an honor.
Many mothers feel unseen and unappreciated in their roles.
Mom Badge aims to help mothers feel recognized and supported.
Community support is crucial for mothers and entrepreneurs alike.
Technology can enhance the way we connect and support each other.
Optimism is about hope, not just positive thinking.
Visual representation of ideas helps others understand your mission.
Trusting in the journey is essential for founders.
Small acts of kindness can have a big impact.
Engaging with others can lead to unexpected opportunities.
Keywords: Mom Badge, Rachel Frosh, startup journey, community support, technology, founder advice, motherhood, digital gift cards, entrepreneurship, mental health, team mom
 
Sound Bites
"92% of moms just do not feel seen."
"Mom Badge is about helping people feel seen."
"You're in a good story."
"It's about inviting people into it."
"Use it, check it out, it's free."
Chapters
00:00 Introduction to Rachel and Mom Badge
02:02 The Journey of Building a Startup
05:30 The Importance of Community and Support
09:28 The Technology Behind Mom Badge
14:49 The Psychology of Risk and Hope
22:38 Advice for Founders and the Importance of Connection
30:21 Engagement and Support for Mom Badge

Jan 7, 2025

32 min

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