In this episode of Disciplined Troublemakers, host Scott Shagory sits down with Pam Prior, a CFO and financial coach with over 30 years of experience. Pam has guided a diverse range of clients, including bootstrapped entrepreneurs, private equity investors, Fortune 500 companies, social media influencers, and professional athletes through the complexities of business finances.

Scott and Pam discuss how tech CEOs, whether bootstrapped or funded, can refine their financial storytelling and address challenges that arise from overlooked financials. Pam shares practical advice on establishing reliable bookkeeping practices, balancing growth with profitability, developing effective pricing models, and determining the right time to bring in a CFO or restructure the team.

For those experiencing uncertainty in their business finances or seeking to implement processes that support sustainable growth, this conversation offers valuable insights and actionable strategies. Learn how to achieve financial clarity and make informed decisions that drive your business forward.

Pam Prior is the owner of a bookkeeping and fractional CFO company, a two-time bestselling author, and the host of the Cash Flow and She Said, She Said podcasts. Known as the "Finance Friend in a Foxhole," she is dedicated to supporting 21st-century entrepreneurs.

Chapters:

00:00 – Introduction
01:03 – "Numbers Reveal Business Story"
05:26 – Financial Literacy: Key to Business Success
09:15 – Early Stage Business Strategy
10:55 – Diversify Investments, Understand Cash Flow
16:11 – Pricing Strategy for Niche Coaching
18:58 – Value over Price
20:02 – "Charging Difficult Clients More"
26:23 – Scaling Beyond Founder Limits
28:29 – Scaling Challenges and Leadership Transition
33:15 – "Importance of Client Contracts"
34:12 – Founder to CEO: Prioritize Roles
38:27 – Family Dynamics in Business Hierarchies
43:04 – Evolving Documentation Practices
45:35 – "When to Hire a CFO"
49:04 – CFO Role in Business Strategy
51:01 – Embracing Entrepreneurial Agility
54:34 – Interview with Pam on YouTube
54:55 – Outro

Quotes:

"Seeing your numbers as your business story clears the fog of uncertainty. That clarity brings true freedom."- Pam Prior

"When uncertainty lifts, clarity and perspective bring confidence and limitless growth."- Scott Shagory

Key Takeaways:

Financials Are Your Business Story, Not Just Numbers
Clean Books Are Cheaper (and Less Stressful) than Cleanups
Lift the Fog: Clarity Equals Confidence
For Bootstrappers: Profit, Scale, and Personal Goals Must Be Balanced
Scaling from $1M to $5M Means Reinventing Processes—and Yourself
Process = Freedom, Not Handcuffs
A CFO Is Your Foxhole Ally, Not Just a Number Cruncher

Connect with Pam Prior

LinkedIn: https://www.linkedin.com/in/pamsprior
Website: https://pamprior.com/

Connect with the Host Scott Shagory:

http://purplefinchgroup.com
http://linkedin.com/in/scottshagory
Email: mailto:[email protected]

Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/

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Welcome back to the Disciplined Troublemakers podcast. In today’s episode, host Scott Shagory engages with Desh Urs, founder and CEO of iBridge —a global leader in digital transformation within healthcare, legal services, utilities, and defense sectors. With over four decades of industry expertise, Desh offers valuable insights into scaling infrastructure and software-as-a-service businesses, reflecting on iBridge 's evolution since its inception in 2004.

The conversation explores the pressing challenges tech companies face in a swiftly evolving environment, focusing on effective data management, the accelerating advancements in AI, and maintaining security in critical industries. Desh discusses strategies for navigating uncertainty, the importance of enduring customer relationships, and the significance of adhering to core company values amidst growth.

Listeners will hear detailed accounts of iBridge 's expansion into international markets like Saudi Arabia, the transition from service-oriented to product-driven models, and how prioritizing both employees and clients has been pivotal to the company's sustained success. This episode provides actionable insights and practical wisdom for CEOs, entrepreneurs, and anyone interested in the transformative role of technology in various industries.

Desh Urs brings a wealth of experience from leading roles at TransUnion, Silicon Graphics, and Acxiom Corp., positioning him as a knowledgeable voice in digital transformation and business scaling.

Chapters:

00:00 - Introduction
01:06 - Understanding and Organizing Data Value
03:22 - Prioritizing Foundational Questions in AI
06:58 - Data Expertise and Security Challenges
12:53 - Saudi Arabia's Social Transformation
14:32 - Rapid Economic Transformation Ahead
17:23 - Customer-Centric Partnership Success Model
22:10 - Customer Trust Ensures Mutual Success
24:21 - Terminating Contract with CEO
28:44 - Conversation Encouragement for Team Awareness
31:04 - Navigating Information Overload Challenges
36:11 - Transitioning from Services to Product
38:13 - Leadership and Transition in Challenges
43:03 - Decision-Making in a Flat Organization
45:08 - Transformative Social Impact of Connectivity
48:12 - Recruitment and Communication Strategy
50:11 - Outro

Quotes:

"Prioritize your customers, understand your true purpose, and embrace vulnerability. That's how we grow together."- Desh Urs

"Ask who you are and who you serve. In a fast-paced world, wisdom comes from reflection and staying true to your mission."- Scott Shagory

Key Takeaways:

Transformation Starts with Understanding Your Data
Adaptability is Essential in an Era of Rapid Change
Security & Trust are Non-Negotiable
Scaling Means Embracing Uncertainty—But Moving Forward Anyway
Partnerships Over Transactions
True Value Lies in Relationships and Integrity
Evolving from Services to Products
Purpose Beyond Profit
Leadership is About Vulnerability and Openness

Connect with Desh Urs:

LinkedIn: https://www.linkedin.com/in/deshurs/
Website:Home - iBridge LLC

Connect with the Host Scott Shagory:

http://purplefinchgroup.com
http://linkedin.com/in/scottshagory
Email: mailto:[email protected]

Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/

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Welcome back to the Disciplined Troublemakers podcast, a space dedicated to navigating the complexities of scaling technology companies with increased efficiency and reduced strain. In this episode, host Scott Shagory engages with Tom Blair, cofounder and CEO of http://iCLERK.AI . Tom brings decades of expertise in AI, data, and enterprise technology, highlighted by successful ventures with Performance Livestock Analytics and ClearAg.

Scott and Tom examine the impact of applied AI on enterprise operations, focusing on how iCLERK optimizes intricate, repetitive workflows in the financial sector through role-aware autonomous agents. Drawing from his extensive experience, Tom discusses the convergence of AI with long-held ideas and how the swift advancements in technology are opening doors for businesses willing to adapt.

Join the conversation as they address the practical challenges and milestones of AI integration, the significance of operational collaborations, and the implications of AI's rapid growth on organizational efficiency, workforce structure, and leadership strategies. For an insightful look into the progression of AI-driven business solutions, this episode provides valuable perspectives.

Chapters:

00:00 - Introduction
00:09 - Automating Financial Reporting with AI
06:04 - Streamlining Workflows in IT Industry
08:17 - "Traceable AI for Reliable Reporting"
10:13 - Career Highlights in AI and Analytics
15:00 - "Tech's Emotional Relief Paradox"
18:48 - Deep Institutional Knowledge in Finance
20:13 - Misconceptions in AI Implementation
24:37 - Leveraging AI for Efficient Learning
27:14 - Joyful Life and Intellectual Fulfillment
32:31 - Early Vision: Semantic Image Recognition
33:43 - Bridging Tech Evolution & Human Static
37:58 - "Startups, Technology, and Happiness Curve"
40:06 - "Quick Results Through Clear Purpose"
42:36 - Outro

Quotes:

"Curiosity drives innovation. Solving real problems brings value and joy."- Tom Blair

"Enhancing a single workflow transforms everything. Technology is about progress and simplicity."- Scott Shagory

Key Takeaways:

Reinventing Professional Workflows, One Agent at a Time
From Fear to Opportunity: AI Adoption Is Accelerating
Scaling Smarter, Not Harder
Depth Matters: Institutional Knowledge as Secret Sauce
AI Implementation Without Disruption
The Joy of Building—and Continuous Learning
The Exponential Future Is Now
Start With Small Steps—And Unlock Big Change

Connect with Tom Blair

LinkedIn: linkedin.com/in/tom-blair
Website: http://www.iclerk.ai

Connect with the Host Scott Shagory:

http://purplefinchgroup.com
http://linkedin.com/in/scottshagory
Email: [email protected]

Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/

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Igor is the co-founder and CEO of Uploadcare. Founded in 2012, Uploadcare is a file loader, data handler, and Content Delivery Network (CDN) – which ensures data is uploaded w/security, compliance, reliable storage, and a friendly UI. The company’s platform saves internal dev teams months of implementation effort. The platform handles 25 billion + requests per week.

The company was acquired by Tiugo Technologies in 2024. Tiugo is a development platform focused on PLG as a GTM and is an affiliate of PSG Equity, a PE buyout firm specializing in mid-market SW companies.

Earlier in his career, Igor founded Riders - an app that helped a million users improve 15 action sports disciplines – such as skateboarding and skiing.

In this episode of The Disciplined Troublemakers podcast, host Scott Shagory engages with Igor to explore the journey of building Uploadcare. They discuss the challenges of the “build vs. buy” decision that CTOs often face, the complexities of managing large-scale file operations for diverse clients, and the strategies for handling unexpected data surges and expanding into international markets. Igor also shares his experience of selling Uploadcare to a private equity firm while preserving the company's mission and maintaining his role as CEO.

This conversation offers valuable insights for founders, technical leaders, and anyone interested in the inner workings of successful SaaS businesses. Discover practical lessons on scaling, leadership, and navigating the evolving tech landscape on The Disciplined Troublemakers.

Chapters:

00:00 - Introduction
01:23 - Tech Scaling Insights with Igor Debatore
05:28 - "Scaling Data Movement Challenges"
08:12 - Forecasting Growth Amid Uncertainty
10:46 - Cloud Platforms' Global Multi-Tenancy Operations
15:41 - Challenges Selling Solutions to Engineers
17:53 - Scaling Challenges in Networking
22:21 - "Founder Experience: Selling a Startup"
26:51 - Finding the Right Financial Partner
27:50 - Positive Experience & Learning Opportunity
31:50 - Reflecting on CEO Journey Transformation
34:24 - Human Connection: A Powerful Catalyst
37:39 - Outro

Quotes:

"I thrive on creating for people and witnessing the joy it brings our team and users. This passion fuels me every day."- Igor Debatur

"Passion projects, where you dive in and take initiative, often spark the greatest impact and fulfillment."- Scott Shagory

Key Takeaways:

Solving Unseen Problems at Scale
From Engineer to Global CEO
Build vs. Buy—Lessons Learned the Hard Way
Automatic Scaling, Real-World Resilience
Acquisition as a Strategic Step, not an End
Staying True to the Core Motivation
The Power of Community and Learning
Advice for Founders and CEOs

Connect with Igor Debatur

LinkedIn: https://linkedin.com/in/debatur
Website: https://uploadcare.com

Connect with the Host Scott Shagory:

http://purplefinchgroup.com
http://linkedin.com/in/scottshagory
Email: mailto:[email protected]

Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/

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In this episode of The Disciplined Troublemakers, host Scott Shagory welcomes Jason Vego, who is the co-founder and CEO of Bevz. Founded in 2020, Bevz is a SaaS platform for independent liquor and convenience stores, helping them centralize and streamline delivery via 3rd party services – such as DoorDash, UberEATS, and GrubHub.

Prior to Bevz, Jason founded a dog grooming SW platform, which failed, and earlier in his career he worked at Citrix as Head of Global Employee Communications and Engagemen

The conversation highlights Bevz's evolution into a comprehensive inventory management system, enabling stores to efficiently track and sell products both in-store and online. Jason discusses the unique challenges of catering to independently operated stores and outlines the company's ambitious growth plans to expand across thousands of U.S. locations. This episode provides actionable insights for technology leaders and retail enthusiasts aiming to scale their businesses and navigate the complexities of the modern marketplace.

Chapters:

00:00 - Introduction
00:09 - Convenience Store Digital Transformation Platform
03:22 - Independent Rural Store Challenges
08:45 - Protein Bar Market Challenges
11:39 - Holistic Approach to Business Growth
15:54 - Snack Food Trends and Market Insights
19:32 - "Building Trust Through Data Insights"
22:54 - "Emphasizing the Human Element in AI"
27:01 - Convenience Retail's E-Commerce Potential
28:14 - Mobile Device Impact on Ordering
32:12 - Scaling Solutions for Tech CEOs
34:09 - Balancing Excel and People Dynamics
40:10 - Leadership Growth and Challenges
41:54 - Value of Fundraising Experience
45:27 - Managing Trade-offs in Business Growth
47:45 - Outro

Quotes:

"Scaling means building trust and empowering overlooked sectors to thrive."- Scott Shagory

"We're transforming independent stores into digital powerhouses, revolutionizing convenience retail."- Jason Vego

Key Takeaways:

Unlocking Potential in the Overlooked
Building Trust and Empowering Growth
Navigating Complexity with Simplicity
Scaling with Product and People in Mind
The Human Touch in a Digital World
Visionary Yet Pragmatic

Connect with Jason Vego:
LinkedIn: https://www.linkedin.com/in/jvego/
Website: https://www.bevz.com/

Connect with the Host Scott Shagory:

http://purplefinchgroup.com
http://linkedin.com/in/scottshagory
Email: mailto:[email protected]

Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/

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Welcome to the Disciplined Troublemakers podcast. In today’s episode, we speak with Jason Young, founder and CEO of Pylon Cybersecurity. Jason Young is the founder and CEO of Pylon Cybersecurity, a firm he started in 2011. Pylon helps security managers automate network compliance through real-time services which ensures data accuracy and a definitive chain of custody.

In 2024 Jason and the team saved the Defense Health Agency, a Combat Support Agency w/in the U.S. DoD that supports medical services readiness for the Army, Navy, and Air Force, $25 million dollars by optimizing their cyber compliance workflows.

Chapters:
00:00 - Introduction
00:09 - Scaling Cybersecurity with Jason Young
03:48 - "From Systems Admin to Auditor"
08:01 - Cybersecurity: Cost Center or Strategic Asset?
12:35 - Transforming Conversations for Meaningful Outcomes
15:48 - Understanding Team-Specific Problems
19:37 - User-Centric Strategy for Agility
20:45 - Listening to Junior Insights
26:42 - Exploring Orchestration Layers in DOD
29:50 - Accidental CEO Journey
31:25 - Effective Leadership and Team Retention
34:16 - Rigid Systems vs. Creative Context
38:11 - Breaking Creative Blocks
43:45 - "Evolving Perceptions and Reality"
45:25 - "Meeting People Where They Are"
47:26 - Outro

Key Takeaways:
Championing Cybersecurity Compliance
Empowering IT Operations
Creating Value with Technology
Culture and Innovation Go Hand in Hand
The Power of Listening

Quotes:
"Turning compliance into a value driver can revolutionize organizations and the entire industry."- Scott Shagory

"Solving the real problem unlocks true innovation and value."- Jason Young

Connect with Jason Young:
LinkedIn: https://www.linkedin.com/in/jason-paul-young/
Website: https://pylonsecure.com

Connect with the Host Scott Shagory:
http://purplefinchgroup.com
http://linkedin.com/in/scottshagory
Email: mailto:[email protected]

Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/

Powered by: http://heartcastmedia.com/

Welcome to another episode of Disciplined Troublemakers, where we explore the landscape of tech companies and the art of scaling businesses effectively. Today, we are joined by Lucas Wilson, CEO of Signpost, who has been steering the company since February 2024 and has achieved remarkable progress.

Signpost supports small and medium-sized businesses in the home service industry by streamlining day-to-day communications with prospects and customers through a unified platform. Lucas offers his perspective on the challenges and opportunities inherent in scaling a SaaS company within the home services sector, as well as the vital role of online reputation management.

Our discussion highlights the importance of quality service as a distinguishing factor and traces Signpost's path toward mastering customer communication. Lucas shares his experiences as a turnaround specialist, emphasizing the need to define a company's core identity and the impact of actively listening to customers.

Join us as we uncover the strategies and insights Lucas contributes, demonstrating why maintaining focus is crucial for growth in today’s rapidly evolving tech landscape. Whether you're a CEO, an entrepreneur, or interested in the mechanics of scaling tech companies, this episode offers valuable takeaways on pursuing progress and excellence.

Chapters:
00:00 - Introduction
01:09 - "Ensuring Quality Customer Communication"
05:53 - "AI and Live Receptionist Integration"
08:05 - Exploring AI Communication Platforms
12:18 - "Uncovering Decision-Making Insights"
15:24 - Improving Customer Service Efficiency
19:16 - Urgent Tornado Warning Tech Support
20:40 - Storytelling and Misunderstandings in Communication
26:07 - Core Values Drive Market Strategy
27:08 - Internal Reflection Drives CEO Success
31:38 - "Empowered Workforce, Secure Future"
35:34 - Enhancing Service Through Technology
36:57 - Franchise Tech Integration Challenges
40:21 - Leadership Roles: Different Mindsets
43:03 - Outro

Quotes:
"Staying focused, listening to our customers, and delivering quality service is what sets us apart."- Lucas Wilson

"Begin with the end in mind, eliminate obstacles, and build trust through seamless communication."- Scott Shagory

Key Takeaways:
Staying True to Core Values
Learning from Experience
Team Empowerment
The Journey of Transformation
Balancing AI and Human Touch
Embracing Challenges as Opportunities

Connect with Lucas Wilson:
LinkedIn: https://www.linkedin.com/in/lukewilsonsignpostceo/
Website: https://bias2action.co/

Connect with the Host Scott Shagory:
http://purplefinchgroup.com
http://linkedin.com/in/scottshagory
Email: mailto:[email protected]

Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/

Powered by: http://heartcastmedia.com/

Melissa Kwan, cofounder and CEO of eWebinar , is transforming webinar automation by eliminating the repetitive strain of live sessions she describes as "soul crushing." In this episode of the Disciplined Troublemakers podcast, Scott Shagory explores how Melissa's innovative solutions enable technology leaders to scale their companies and boost profitability. Beyond eWebinar, Melissa cohosts the Profit-Led podcast, sharing growth strategies for bootstrap founders, and offers valuable insights on startup life and founder well-being on LinkedIn. The conversation delves into scaling product-led growth tech companies, Melissa’s journey toward building a lifestyle business, and her unique approach to redefining success on her own terms.

Chapters:

00:00 - Introduction
01:22 - Scaling Insights with Melissa Kwan
04:59 - "Scaling Tech Companies: Growth Path"
07:32 - Uncertain Investment in SEO
12:02 - "LinkedIn Strategy Amid Algorithm Shifts"
14:17 - Navigating Relationships in a PLG World
19:08 - Customer Churn Feedback Request
21:03 - Clear Prioritization and Trade-Offs
24:07 - Market Misunderstanding Inquiry
26:52 - Live Content: What Truly Needs It?
31:40 - "Persistence in Sales and Marketing"
34:31 - Lifestyle Business Decision: Moment or Gradual?
36:26 - Customers Over Investors
41:04 - Finding Freedom Through Self-Understanding
43:43 - The Mental Struggles of Founders
47:27 - Breaking Free from Traditional Expectations
50:03 - Defining Personal Meaning and Connection
52:40 - Outro

Key Takeawys:

eWebinar Platform Overview
Ideal Customer Profile for eWebinar
Challenges and Opportunities in Scaling
LinkedIn and SEO Strategies
Balancing PLG and Customer Relationships
Misunderstandings in the Market
Personal and Professional Growth as a CEO
Transformation and Happiness in Business

Quotes:

"Don't leave a thriving community to chase someone who doesn't value you. Focus on those who appreciate your presence."- Melissa Kwan

"Know your goals and choose your path wisely. Embrace the freedom to create the life you desire."- Scott Shagory

Connect with Melissa Kwan:
LinkedIn
Website

Connect with the Host Scott Shagory:
Website
LinkedIn
Email: [email protected]

Sponsor: Purple Finch Group
Call to Action: Visit eWebinar
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In this episode of the Disciplined Troublemakers podcast, host Scott Shagory speaks with Roberto Penacastro Ortega, founder and CEO of LeadSales. Since its inception in 2020, LeadSales has provided a CRM and conversational commerce platform that assists small and medium-sized businesses in Latin America with lead management and generation through social media. Roberto discusses the challenges and opportunities of scaling SaaS companies in the region, the role of conversational commerce, and his vision to position LeadSales as one of Mexico's leading tech firms. Explore the future of lead generation and the impact of conversational commerce on business growth.

Quotes:

"Transitioning to exponential growth is achievable with less effort and stress."- Scott Shagory

"With millions of daily messages, we have the data to harness AI effectively."- Roberto Penacastro Ortega

Chapters:

00:00 - Introduction
01:30 - Future of Conversational Commerce
03:40 - Mobile-Only Challenges in CRM Markets
07:55 - Asynchronous vs. Real-Time Communication
12:19 - From Family Business to Tech Startup
16:53 - Rapid Startup Growth Strategy
20:35 - "Keys to Successful Team Dynamics"
21:52 - "Scaling Tech CEOs with Strategy"
25:59 - Unlocking Global Potential for SMBs
27:54 - Unlocking Implicit Genius
31:26 - Leadership Handoff Challenges and Opportunities
35:15 - Navigating Challenges and Transformative Moments
39:23 - Startup Challenges Outside the US
42:41 - LinkedIn's Global Connectivity Benefits
44:39 - Outro

Featured in this Episode:
Roberto (Roby) Penacastro Ortega is the founder and CEO of LeadSales. Founded in 2020, LeadSales is a CRM platform that helps businesses generate and manage leads. Their focus is helping small and medium businesses in LATAM manage all their potential sales via social media channels by centralizing leads into column chats.

Connect with Roby:
LinkedIn
Website

Connect with the Host: Scott Shagory
Website
LinkedIn
Email: [email protected]

Sponsor: Purple Finch Group
Call to Action: Visithttps://leadsales.io/en/
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Ganesh Padmanabhan is the founder and CEO of Autonomize AI, which utilizes AI Agents and Copilots in healthcare workflows by summarizing unstructured healthcare data for data-driven decision making and improved patient outcomes. Autonomize AI is backed by healthcare VC firm AMV and tech VC firm ATX Venture Partners.

Prior to Autonomize AI, Ganesh helped scale AI companies such as Molecula and CognitiveScale and before that time spent at Dell and Intel.

Quotes
"Choose a meaningful problem, ensure people are willing to pay for the solution, and build a sustainable business." — Ganesh Padmahaban

"At the core of everything is the patient. By organizing their data and understanding their journey, we can revolutionize healthcare and create meaningful efficiencies." — Ganesh Padmahaban

Featured in this Episode:
Ganesh Padmahaban
LinkedIn: https://www.linkedin.com/in/padmanabhan
Website:https://autonomize.ai/

Sponsor:
Purple Finch Group

Host:
Scott Shagory
Email: [email protected]
Website: http://purplefinchgroup.com

Chapters:
00:00 - Introduction
03:36 - Healthcare's Unstructured Data Challenge
08:27 - Patient-Centric Health Data Platform
11:56 - AI's Role in Healthcare Relief
14:10 - "Conviction in Meaningful Problem Solving"
17:24 - Recruiting and Building Company Culture
22:38 - AI Impact and Misunderstandings
24:27 - "Delivering Clear, Real-World Value"
28:56 - Learning Through Customer Interaction
31:34 - Service for Others' Aspirations
34:59 - Balancing Tech and Sales Enablement
37:58 - CEO Evolution and Team Dynamics
42:27 - Resilience in Leadership Challenges
45:11 - Seeking Support for Aggressive Growth
46:32 - Hiring & Strategic Partnerships Focus
50:27 - Outro

Call to Action Links:
Visit http://Autonomize.ai

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