Business Owners Unfiltered

By BestBonobos

Listen to real stories from real founders navigating one of life's biggest decisions: selling their business.

Most business owners only exit once or twice in their lifetime, but the process

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FAQs about Business Owners Unfiltered:

How many episodes does Business Owners Unfiltered have?

The podcast currently has 9 episodes available.

Business Owners Unfiltered episodes:

May 11, 2026 Business Owners Unfiltered Episode 8: Kathryn Smith on The Hidden Hardships of Entrepreneurship
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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37min
April 29, 2026 Business Owners Unfiltered Episode 8: Roman Rodomansky on Building a Culture-First Tech Company
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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24min
April 23, 2026 Business Owners Unfiltered Episode 7: Andrew Yasynyshyn on Outsourcing in the Age of AI
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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32min
April 16, 2026 Business Owners Unfiltered Episode 6: Stever Robbins on Business Scaling Without Chaos
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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29min
April 07, 2026 Business Owners Unfiltered Episode 5: Bob Graham on Mastering Business Storytelling
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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29min
March 31, 2026 Business Owners Unfiltered Episode 4: Robert Jordshaugen on Transforming Healthcare
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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32min
March 25, 2026 Business Owners Unfiltered Episode 3: Sebastiaan Winter on Unlocking Entrepreneurial Success
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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21min
March 18, 2026 Business Owners Unfiltered Episode 2: Brian Judson on Navigating Business Sales From a Broker
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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28min
March 11, 2026 Business Owners Unfiltered Episode 1: Elias Crum on Revolutionizing Small Business Exits with AI
This episode is brought to you by BestBonobos, the AI-powered platform to help you sell your business yourself.
Today, we spoke with Elias Crum, co-founder of BestBonobos.
Discover how he began a new venture aimed at empowering small business owners after realizing the unfairness of the status quo. Elias reveals the secrets to preparing your business for a successful sale, using innovative AI tools to simplify the process. Learn how to accurately value your company, create compelling sales materials, and navigate the emotional aspects of selling your life's work.
Timestamps:
00:00 - Who is Elias Crum and why you should listen
02:10 - The power of early preparation before selling
05:28 - The hidden costs brokers charge and how to beat them
12:00 - How AI is transforming small business valuation
17:39 - The end-to-end process for selling your business yourself
20:49 - Avoiding the lowball trap with proper data preparation
25:40 - Addressing AI skepticism and ensuring accuracy in valuations
29:43 - Why Atlanta was chosen for the launch of Best Bonobos
33:12 - The partnership story with Sebastian and market gaps filled
39:00 - The bold message: Start preparing today for a better tomorrow

Links:
Connect with Elias 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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41min

FAQs about Business Owners Unfiltered:

How many episodes does Business Owners Unfiltered have?

The podcast currently has 9 episodes available.