What does it really take to scale a company from zero to over 1,000 employees with leadership rooted in kindness -- without burning out your people or yourself?

In this episode of The Business Philosopher Within You, host Bhavesh Naik sits down with Ilya Vinogradsky, Founder, CTO, and Board Member of Astound Digital, to explore what he calls The Kindness Principle—a people-first leadership philosophy that helped him grow a global organization through booms, busts, acquisitions, and massive complexity.

Ilya has spent over two decades building and scaling digital businesses. Starting in the early days of e-commerce, he grew Astound from a small founding team into a global digital consultancy with 1,000+ employees, 600+ certified engineers, 3,000+ solutions delivered, and over $10 billion in customer value created.

But this conversation isn’t about tactics alone.

It’s about how leadership must evolve as scale increases—and why kindness, culture, and human-centered decision-making become more important, not less.

In this conversation, we explore:

• What changes—and what must not—when you scale from 10 to 1,000 people

• Why culture is always driven top-down (and cannot be delegated)

• How to build systems and processes without dehumanizing the organization

• The real role of the CEO in shaping culture during growth and acquisitions

• Why taking care of people first ultimately strengthens clients and the business

• How personal inner growth and leadership maturity are inseparable

• What it means to lead with heart while still making hard decisions

At its core, this episode is about applied business philosophy.

Not abstract values.

Not posters on the wall.

But philosophy translated into daily decisions, leadership behavior, and organizational design—especially under pressure.

If you’re a founder, CEO, or leader who wants to build a business that can scale beyond you and outlive you, this conversation will challenge how you think about leadership, culture, and success.

If this conversation resonates with you:

📌 Subscribe/follow for future conversations with founders and business philosophers

💬 Share your thoughts or questions in the comments—we learn from each other

Episode Show Notes and Deep Dive:

📚 Deep Dive, Show Notes and Reference Reading: https://www.awayre.com/scaling-kind-leadership-0-1000-employees/

Connect with Ilya Vinodradsky and Astound Digital:

🔗 Linkedin: https://www.linkedin.com/in/vinograd/

🌐 Website: https://astounddigital.com/

🎞 YouTube Channel: https://www.youtube.com/@AstoundDigital

"The Business Philosopher Within You" Podcast:

🎬🎙️📖 Website: https://www.awayre.com/business-philosopher-within-you-podcast/

🦸‍♀️Be a Guest: https://www.awayre.com/business-philosopher-within-you-podcast-guest/

🤔 Podcast: The Business Philosopher Within You Podcast

🗓️ Published: 2nd & 4th Wednesdays

📇 Episode: 35

📜 Format: Full Episode

📅 Date: February 11, 2026

👨‍💼 Guest: Ilya Vinogradsky, Founder, CTO, Astound Digital

🎙️ Host: Bhavesh Naik

CHAPTERS:

00:00 - Highlights and Introduction

03:54 - Astound Digital: Naming the Company

13:31 - Identifying the Customer Base

18:41 - Journey to Success

24:24 - Company Culture Insights

28:20 - Cultural Blueprint Dynamics

32:15 - HR's Role in Company Culture

33:59 - Organizational Structure Explained

37:09 - Depth of the Organizational Structure

38:36 - Promises and Perils of Company Acquisitions

42:57 - Future Vision for Astound Digital

45:49 - Advice for Successor Leadership

47:50 - Impact of AI on the Marketplace

52:02 - Advice to Younger Self

54:36 - Evolution of the Company

58:23 - Personal Grounding Principles

1:00:59 - Getting In Touch and Parting Words

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Music by Yrii Semchyshyn (Thank You!): https://www.patreon.com/yuriisemchyshyn

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What does it take to build a company that performs at the highest level, and stays human at the core?

In this second part of my conversation with Mike Chaput, CEO of Endsight, we go beyond values-driven culture and explore the disciplines, systems and operational rhythms that make an organization truly self-sustaining.

Mike’s journey -- buying his first business at 24 with borrowed money, failing, rebuilding, and ultimately creating one of the top-performing IT support companies in the country -- gives him a rare, grounded perspective on what “enduring success” actually looks like.

Today, Endsight is a 140-person company generating $35M+ in annual revenue with a 20% EBITDA margin, putting it in the top 1% of its industry. But the most extraordinary part? Mike built it through people-first leadership, relentless clarity on core values and a deep commitment to operational excellence.

In this episode, we explore:

• Why memorable, clear, branded, and complete core values become the operating system of a healthy business

• The RSVP values framework: Respect & Connect, Servant’s Heart, Value Value, and Progress Over Comfort

• How Endsight hires for culture first, even before skills

• Using lifeline interviews to uncover ethics, motivations, and alignment

• Why avoiding a bad hire is more valuable than landing a good one

• How constraints create freedom, and why discipline unlocks creativity

• The rhythms, systems, and lean practices that operationalize excellence

• How to build a culture where people naturally take ownership and solve problems

• What leaders must understand about motive, followership, and sustainable influence

If you’re a founder, a CEO, or a leader who wants to build a company that outlives you, this conversation is full of gold.

📌 If this episode sparks insight or challenges your thinking, leave a question or reflection in the comments. This community grows through the questions we ask together.

Like, subscribe, share, and most importantly… keep asking better questions.

Episode Show Notes and Deep Dive:

📚 Deep Dive, Show Notes and Reference Reading: https://www.awayre.com/activate-company-culture-playbook/

Connect with Mike Chaput:

🌐 Website: https://www.endsight.net

🔗 Linkedin: https://www.linkedin.com/in/michaelchaput/

🎞 YouTube Channel: https://www.youtube.com/@thechaputperspective

"The Business Philosopher Within You" Podcast:

🎬🎙️📖 Website: https://www.awayre.com/business-philosopher-within-you-podcast/

🦸‍♀️Be a Guest: https://www.awayre.com/business-philosopher-within-you-podcast-guest/

🤔 Podcast: The Business Philosopher Within You Podcast

🗓️ Published: 2nd & 4th Wednesdays

📇 Episode: 34

📜 Format: Full Episode

📅 Date: November 26, 2025

👨‍💼 Guest: Mike Chaput, Founder and CEO, Endsight

🎙️ Host: Bhavesh Naik

CHAPTERS:

00:00 - Highlights and Introduction

02:35 - Creating an Executable Value System

09:31 - Core Values as Constraining Behaviors

15:16 - Hiring for Culture and Values Vs Skill

23:06 - Cultural Orientation After Hiring

25:54 - Operationalizing Company Culture

31:41 - Achieving 20% Profit Margins

35:49 - Non-Negotiables for Success

40:43 - Impact of AI on the Future

46:08 - Human Vs AI: Insights, Perspectives and a Prediction

47:24 - Darkest Moment Reflection

53:55 - Finding Peace and Inspiration

56:45 - Lasting Words of Wisdom and Getting In Touch

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Music by Yrii Semchyshyn (Thank You!): https://www.patreon.com/yuriisemchyshyn

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Is it possible to scale a company to substantial revenues while nurturing a truly values-driven, people-centric culture without sacrificing purpose?

In this episode of "The Business Philosopher Within You," host Bhavesh Naik sits down with Mike Chaput, CEO of Endsight, to explore this compelling question. Mike shares his journey from the founding of Endsight to its current success, emphasizing the significance of a people-centric culture and the alignment of vision with daily operations.

Tune in and you will develop your own unique insights into how a well-crafted vision can include all stakeholders, creating a win-win scenario for everyone involved.

Mike discusses the iterative nature of core values and how they guide company culture and decisions. He also fleshes out the pros and cons of setting Big Hairy Audacious Goals (BHAGs) to inspire and motivate teams.

• The role of vision in inspiring employees and stakeholders
• Strategies for engaging employees and executing strategic plans
• The impact of one-on-one meetings on organizational culture
• How accountability drives performance and growth

Join us as we uncover the secrets to building a high-performing organization that stands the test of time. Tune in to discover how you can apply these principles to your own business journey.

Episode Show Notes and Deep Dive:

📚 Deep Dive, Show Notes and Reference Reading: https://www.awayre.com/scale-revenue-values-leadership-ceo-lessons/

Connect with Mike Chaput:🌐 Website: https://www.endsight.net🔗 Linkedin: https://www.linkedin.com/in/michaelchaput/

"The Business Philosopher Within You" Podcast:

🎬🎙️📖 Website: https://www.awayre.com/business-philosopher-within-you-podcast/

🦸‍♀️Be a Guest: https://www.awayre.com/business-philosopher-within-you-podcast-guest/

🤔 Podcast: The Business Philosopher Within You Podcast

📇 Episode: 33

📜 Format: Full Episode

📅 Date: November 12, 2025

👨‍💼 Guest: Mike Chaput, Founder and CEO, Endsight

🎙️ Host: Bhavesh Naik

CHAPTERS:

00:00 - Highlights and Introduction

03:34 - The Origin of Endsight

06:45 - Understanding Vision in Business

13:28 - Inclusive Vision for Success

16:22 - Leadership as a Follower of Vision

20:20 - Setting Big Hairy Audacious Goals

22:14 - Employee Engagement Strategies

25:28 - Vision at the Start of Endsight

29:35 - Vision, Direction, Lean Practices and Quality Control

34:36 - Bringing Vision to Daily Operations

38:28 - Executing the Strategic Plan

41:15 - Importance of One-on-One Meetings

45:33 - Accountability as a Leadership Tool

51:21 - Accountability Practices at Endsight

55:33 - Defining Core Values

57:50 - Embracing the Business Philosopher Mindset

59:36 - Identifying Core Values

1:08:27 - End of Part 1: Vision and Values | Part 2 Covers: Strategies and Disciplines

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Music by Yrii Semchyshyn (Thank You!): https://www.patreon.com/yuriisemchyshyn

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