• Business Owners Unfiltered Episode 8: Kathryn Smith on The Hidden Hardships of Entrepreneurship
    May 11 2026

    This episode is brought to you by BestBonobos, the AI-powered platform to help you sell your business yourself. Today, we spoke with

    Today, we spoke with Kathryn Smith, founder of Walton Birch, specializing in web development and marketing consulting. We dive into why most depictions of entrepreneurship are off the mark, the importance of understanding exit strategies from day one, the real skills that matter for new entrepreneurs, and more.

    Timestamps:

    00:00 - Welcome & why entrepreneurship isn’t what you think 01:01 - Kathryn's unlikely journey from corporate to CEO 02:33 - The unpredictable, messy reality of starting a business 03:09 - Common misconceptions about entrepreneurs in popular culture 04:17 - Why most depictions of entrepreneurship are inaccurate 05:24 - Is entrepreneurship teachable? Lessons from an MBA 07:02 - The romanticized vision vs. the real grit of entrepreneurship 08:02 - Changing social views on side hustles and small businesses 09:00 - Challenges faced when starting a service-based business 11:46 - The importance of planning for exit from the beginning 12:39 - How to recognize the value of your business early on 13:39 - Exit planning as a crucial part of your business model 14:08 - Building a brand separate from yourself for future sale 15:08 - The overlooked value in business preparation and mindset 16:26 - How conversations can reveal hidden business potential 17:19 - Staying flexible and continuously pivoting your business 18:07 - Mentorship, giving back, and supporting the next generation 19:16 - The struggle of starting from scratch and why education helps 21:25 - Dispelling fears around not knowing enough skills 22:44 - Essential business knowledge: finance, marketing, legal 25:20 - Sales as a core skill for service entrepreneurs 27:12 - Networking, relationships, and making sales in a service business 28:47 - Constantly being in “sales mode” as an entrepreneur 30:17 - The value of coaching clients directly through social platforms 32:09 - Leveraging podcasts to build trust and attract clients 33:35 - The power of visibility and relationship-building through podcasting 34:26 - Preparing to exit: why intentional planning is key 36:00 - Summing up: Be bold, be strategic, plan your exit early 37:00 - Resources & how to connect with Kathryn and BestBonobos Resources & Links: Walton Birch: https://waltonbirch.com/ Kathryn Smith on LinkedIn: https://www.linkedin.com/in/kathrynrsmith/ Thank you so much for listening. If you want a free valuation of your company and a step-by-step platform on how to sell your business yourself by yourself before committing to brokers, sign up for BestBonobos today here at https://bestbonobos.com/

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    36 mins
  • Business Owners Unfiltered Episode 8: Roman Rodomansky on Building a Culture-First Tech Company
    Apr 29 2026

    This episode is brought to you by BestBonobos, the AI-powered platform to help you sell your small business yourself. Today, we spoke with Roman Rodomansky, COO and Co-founder of Ralabs, a software development company originating in Ukraine. We're diving deep into Roman's transition from engineering to entrepreneurship over 10+ years, the highs and lows of his various ventures, and all the lessons he learned along the way, like how important values and culture is when curating his team. Timestamps: 00:00 - Introducing Roman Rodomansky and his entrepreneurial background

    00:16 - Roman’s decade-long journey from engineering to founding businesses

    01:19 - Offline vs online mindset: The engineer’s dream of tactile creation

    02:08 - Experiments with retail and offline shops — what worked and what didn’t

    03:18 - The role of AI in differentiating modern businesses

    04:28 - Why offline presence still holds value in a digital world

    05:47 - The flower subscription venture: Breaking down why it failed

    06:47 - The challenges of scaling a local flower shop into a nationwide business

    07:40 - Cultural nuances in consumer demand for flowers and occasions

    09:07 - Learning from early ventures: The value of experience over ROI

    09:22 - Roman’s flagship company, Rallops: Building a web and AI-driven service firm

    10:15 - The culture of innovation and team empowerment at Rallops

    11:26 - How to foster honesty and boldness in client-facing teams

    12:38 - The company's client-first philosophy and unique problem-solving approach

    13:40 - The importance of knowledge sharing within a tech company

    14:16 - Hiring, nurturing, and evolving a 150-person team in Ukraine

    16:15 - Continuous learning and the role of AI in Roman’s growth journey

    17:02 - What Roman is currently learning: Focus on AI and new tech trends

    17:31 - Roman’s experience in teaching and volunteering to educate future developers

    20:15 - The rewarding stories of students transitioning into IT careers

    22:21 - Wrapping up: Future discussions, part two, and ongoing stories Resources & Links: Ralabs: https://ralabs.org/ Ralabs Monthly AI Digest Podcast: https://youtube.com/playlist?list=PL_y083Co1bbBXj9LeoOzKEgJhtjnJ-xAL&si=mO0kNKMC4VREDfT6 Roman Rodomansky on LinkedIn: https://www.linkedin.com/in/rodomansky/

    Thank you so much for listening. If you want a free valuation of your company and a step-by-step platform on how to sell your business yourself by yourself before committing to brokers, sign up for BestBonobos today here at https://bestbonobos.com/

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    23 mins
  • Business Owners Unfiltered Episode 7: Andrew Yasynyshyn on Outsourcing in the Age of AI
    Apr 23 2026

    This episode is brought to you by BestBonobos, the AI-powered platform to help you sell your business yourself. Today, we spoke with Andrew Yasynyshyn, CEO and Co-founder of Ralabs, a software development company (the one who built BestBonobos actually). We're diving deep into how outsourcing, especially amidst the AI revolution, can skyrocket your business growth, making it faster, smarter, more scalable. If you're tired of slow growth and endless hiring hassles, this episode is your wake-up call! Timestamps:

    00:00 - Introduction to outsourcing for small businesses and SaaS founders

    00:36 - How Best Bonobos chose outsourcing to build their platform 01:33 - Andrew shares insights on his background and music instruments

    02:37 - The significance of cultural fit when outsourcing globally

    03:55 - How to approach outsourcing versus building in-house

    04:12 - Key factors like geography, culture, and long-term partnership 05:05 - Rational decision-making in outsourcing

    06:08 - The pitfalls of hiring freelancers and the value of outsourcing companies

    07:09 - The importance of company culture and communication

    08:04 - Outsourcing options in Europe, Asia, and South America

    09:01 - How cultural differences affect remote work expectations

    10:29 - Direct feedback, transparency, and integrity in outsourcing relationships

    11:32 - Common mistakes including lack of face-to-face interaction and budget mismatch

    12:24 - The importance of thorough vendor research and presence of technological expertise

    13:22 - How to avoid failures by selecting transparent, aligned outsourcing partners

    14:25 - The danger of rushing hiring decisions and lack of options

    15:21 - The importance of human connection in outsourcing success 16:12 - Risks of automating away critical roles—like security and customer service

    17:27 - Focus on client relations, face-to-face engagement, and trust-building

    18:42 - Evaluating outsourcing partners based on recent tech agility and updates

    21:14 - How staying on top of AI tech makes outsourcing more strategic and scalable

    23:12 - Andrew's insights on AI's rapid evolution and its impact on outsourcing

    27:36 - Final insights: AI enables faster scaling and higher company valuation

    28:03 - Practical steps to boost development productivity this week 29:02 - The importance of human oversight in AI-driven development 30:14 - Preparing your team for the next leap in software speed and security Resources & Links:

    Ralabs: https://ralabs.org/

    Andrew's newsletter: https://ralabs.org/updates-from-the-ceo-who-codes/

    Andrew Yasynyshyn on LinkedIn: https://www.linkedin.com/in/andrii-yasynyshyn/ Thank you so much for listening. If you want a free valuation of your company and a step-by-step platform on how to sell your business yourself by yourself before committing to brokers, sign up for BestBonobos today here at https://bestbonobos.com/

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    32 mins
  • Business Owners Unfiltered Episode 6: Stever Robbins on Business Scaling Without Chaos
    Apr 16 2026

    This episode is brought to you by BestBonobos, the AI-powered platform to help you sell your business yourself.

    Today, we spoke with Stever Robbins, CEO of Stever Robbins, Inc. where he provides one-on-one coaching, group programs, and keynote speeches, focusing on helping small business owners, entrepreneurs, and consultants become known in their communities. Stever is a seasoned startup veteran and angel investor with extensive experience in scaling businesses, having been involved in four IPOs and one acquisition.

    This episode explodes myths around scaling, revealing raw truths from a startup veteran and master of chaos management. If you've ever felt overwhelmed by growth or wondered how to prepare your business for sale, this is your wake-up call.

    Timestamps:

    00:00 - How chaos accompanies fast growth and what structure you need 00:31 - Steve Robbins’ background in startups and rapid scaling experiences 01:48 - The hyper-growth of a volunteer event and chaos management 02:46 - Managing volunteers versus employees: What’s different? 03:42 - The cultural and emotional investment in volunteer organizations 05:33 - Why many startups break when they try to scale 06:16 - The system breakdown for scaling from 3 to 100+ employees 07:11 - The importance of systems and processes that scale 08:38 - Designing processes for customer support, accounting, and operations 10:04 - How to identify and document key processes early 11:28 - Making your business run without you and preparing for sale 12:45 - The general functions every scalable business needs 13:42 - The importance of onboarding and documenting procedures 14:43 - How to delegate up the management ladder effectively 15:47 - The importance of allowing leaders to step back and let the business run 16:33 - The playbook of big CEOs: Fire fast and hire right 17:18 - The pitfalls of holding onto wrong talent too long 18:21 - The biggest operational mistake in hiring and how to fix it 19:20 - Using trial periods to assess fit and proactively measure soft skills 20:34 - The danger of prioritizing buzzwords over real value 21:02 - Building enterprise value with long-term, stable growth 22:08 - The obsession with gaming valuation and startup hype 23:07 - How investors and founders can manipulate multiple valuation systems 24:03 - The influence of buzzwords like AI and “tech” in valuation games 25:36 - Why thinking like a value investor is the secret to enduring success 26:16 - The free tool to evaluate your company’s true worth 27:17 - Wrapping up and how to connect with Steve Robbins

    Resources & Links:

    Check out the Stever Robbins, Inc. website

    Connect with Stever Robbins on LinkedIn

    Thank you so much for listening. If you want a free valuation of your company and a step-by-step platform on how to sell your business yourself by yourself before committing to brokers, sign up for BestBonobos today here at https://bestbonobos.com/

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    29 mins
  • Business Owners Unfiltered Episode 5: Bob Graham on Mastering Business Storytelling
    Apr 7 2026

    This episode is brought to you by BestBonobos, the AI-powered platform to help you sell your business yourself.

    In this episode, Bob Graham, CEO of SpearPoint Ink, takes us on a rollercoaster journey from his roots in journalism to creating authority-building books that transform businesses.

    Timestamps: 00:00 - Transforming your story: from journalist to business authority 02:44 - Why telling your story is the foundation of marketing 04:12 - The mistake most entrepreneurs make in messaging 05:28 - Building authority that amplifies your business value 07:05 - How process documentation boosts scalability and valuation 09:16 - The truth about business valuations and exit strategies 12:00 - How storytelling connects deeply with your audience 14:01 - AI as a tool for process refinement and documentation 15:50 - The unlearning process: ditching people-pleasing for growth 17:45 - How to realistically evaluate your business's worth 20:36 - Why most business owners overestimate their company's value 22:35 - Building a brand that sells — and why early focus matters 23:55 - The power of bold opinions and unapologetic authenticity 26:23 - Embracing your unique path and resisting crowd opinions 27:16 - Final thoughts: owning your narrative and preparing for exit Check out SpearPoint Ink, and connect with Bob on LinkedIn! Thank you so much for listening. If you want a free valuation of your company and a step-by-step platform on how to sell your business yourself by yourself before committing to brokers, sign up for BestBonobos today here at https://bestbonobos.com/

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    29 mins
  • Business Owners Unfiltered Episode 4: Robert Jordshaugen on Transforming Healthcare
    Mar 31 2026

    This episode is brought to you by BestBonobos, the AI-powered platform to help you sell your business yourself.

    Today, we spoke with Robert Jordshaugen, founder and CEO of Breakthrough6 and Neurabello and co-founder and CIO of KindBridge Inc.

    This episode dives deep into the raw truths of building innovative healthcare startups while balancing mental resilience. Robert Jordshaugen shares his journey tackling industry obstacles, the importance of mental health, and how to truly prepare for fundraising and scaling success.

    Timestamps:

    00:00 - Welcome and introduction: the journey from healthcare consulting to groundbreaking startup

    00:36 - Robert’s background: from gambling addiction aid to depression breakthrough

    01:59 - The mission behind Breakthrough Six: revolutionizing depression treatment

    02:20 - What attracted Robert to entrepreneurship in healthcare 02:45 - The ups and downs of entrepreneurial life and mental health management

    03:31 - Overcoming stress and challenges: staying mentally resilient 04:30 - The reality of investor communications and bad news timing 05:47 - The importance of organized data and due diligence in funding 07:01 - Creating new markets and recognizing opportunities in healthcare

    08:42 - Mission focus: tackling the 48 million Americans with treatment-resistant depression

    09:44 - Innovations in brain stimulation treatments and fast-impact protocols

    11:22 - How B6 is disrupting traditional psychiatry practices with targeted treatments

    13:01 - The power of quick, effective treatment for depression and PTSD 15:39 - Entrepreneurial burnout and signs that founders should watch for 16:33 - Common mental health struggles among entrepreneurs

    17:35 - The obsession and obsession-driven nature of entrepreneurs 18:26 - Habits to stay grounded: practicing resilience and connection 19:53 - The importance of organization and backup plans in funding 20:50 - Behind-the-scenes of funding timelines and relationship-building with investors

    22:31 - How to prepare for and navigate fundraising cycles

    23:01 - Building trust and making investment easy through organizing data

    24:25 - Crafting an elevator pitch and the importance of storytelling 26:35 - The value of practicing presentations and networking face-to-face

    28:08 - Lessons learned the hard way: persistence, connection, and face-to-face meetings

    29:58 - Final advice

    30:53 - Closing remarks

    Check out Robert's businesses:

    KindBridge: https://kindbridge.com/

    Breakthrough Six: https://www.breakthrough6.com/

    Neurabello: https://www.neurabello.com/

    Connect with Robert on LinkedIn: https://www.linkedin.com/in/robert-jordshaugen-mba-76335b/

    Thank you so much for listening. If you want a free valuation of your company and a step-by-step platform on how to sell your business yourself by yourself before committing to brokers, sign up for BestBonobos today here at https://bestbonobos.com/

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    31 mins
  • Business Owners Unfiltered Episode 3: Sebastiaan Winter on Unlocking Entrepreneurial Success
    Mar 25 2026

    This episode is brought to you by BestBonobos, the AI-powered platform to help you sell your business yourself.

    Today, we spoke with Sebastiaan Winter, co-founder of BestBonobos.

    What does collecting Christmas trees have to do with selling a business? More than you’d think. In Episode 3, BestBonobos co-founder Sebastiaan Winter takes us through his entrepreneurial journey, from childhood hustles to tackling one of the biggest blind spots in small business ownership: knowing when and how to exit.

    Timestamps: 0:01 - Intro & welcome 0:39 - Sebastiaan’s background & early hustles 2:06 - Growing up around family businesses 2:58 - Realizing he was “cut for it” 3:19 - Why partner up instead of going solo 4:25 - Where he gained the most knowledge 6:21 - Surrounding yourself with the right people 6:35 - What inspired Best Bonobos 7:45 - How Best Bonobos differs from traditional valuation 8:50 - Lessons learned building with AI 9:46 - Why selling a business is harder than people think 12:06 - Biggest challenge: getting the message out 13:07 - Vision for the future 14:17 - When to start thinking about exit readiness 15:25 - Practical steps to prepare your business for sale 17:05 - How to emotionally prepare for an exit 17:36 - The mindset that carries him through 18:20 - Final advice for entrepreneurs 18:51 - Closing & how to get on the podcast 20:10 - Outro

    Connect with Sebastiaan on LinkedIn

    Get a free valuation for your company at bestbonobos.com to maximize the value of your sale at minimal cost.

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    20 mins
  • Business Owners Unfiltered Episode 2: Brian Judson on Navigating Business Sales From a Broker
    Mar 18 2026

    This episode is brought to you by BestBonobos, the AI-powered platform to help you sell your business yourself. Today, we spoke with Brian Judson, senior business broker at Best Business Brokers.

    Ever wondered what really goes into selling a business? Today, we dive deep with Brian Judson, seasoned business broker of almost 19 years. Brian talks to us about why overpricing a business sabotages your sale before it begins, how emotional readiness influences successful business exit strategies, the impact of networking and community engagement on deal flow, and more.

    Timestamps: 00:00 - Introduction to Brian Judson: The broker behind the scenes 02:00 - What attracted Brian to become a business broker? 03:34 - Defining the broker as a gatekeeper and relationship builder 04:15 - How brokers filter unqualified buyers effectively 05:24 - The importance of understanding your client’s mandate and fit 07:13 - Common missteps owners make when selling their business 08:16 - How delegating and planning can drastically improve sale value 09:16 - The emotional side of selling and mental readiness 10:14 - Approaching owners ready to retire: Planning early 12:27 - Navigating the emotional challenges of business exit 14:00 - The reality of valuation myths and misconceptions 15:41 - How offers often get lowballed during due diligence 16:34 - Pricing strategies: When flexibility is key 17:05 - Subjectivity in valuation and multiples in practice 18:03 - Lessons learned from overestimated business value 19:01 - Overpricing: Risks and warning signs in the market 19:58 - What experts overlook about business stability and culture 21:20 - The power of networks and platforms like BizBuySell 23:09 - The future of brokerage with AI and automation 25:32 - Final advice: Start planning early, 2-3 years ahead 26:13 - What makes a business truly valuable? 27:10 - The importance of community involvement for brokers Links: Connect with Brian Judson on Linkedin. Get a free valuation for your company here to maximize the value of your sale at minimal cost here at the BestBonobos website.

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    28 mins