In this episode of Startup Therapy, co-hosts Sandeep Shroff and Gaurav Rastogi dive deep into the rollercoaster journey of Sandy, the founder and CEO of Innovaccer. The episode begins with a vivid metaphor comparing the startup experience to a rollercoaster ride—slowly climbing up, facing sudden drops, and the uncertainty of what lies ahead. Sandy shares his remarkable journey from starting with a Wharton-Harvard data project to achieving an impressive $180 million in annual recurring revenue (ARR) after experiencing significant ups and downs, including a drop from $10 million to $1 million.Sandeep and Gaurav, highlighting their shared connection with Sandy through their alma mater, IMA. Gaurav expresses his excitement about having Sandy on the podcast, emphasizing the fascinating nature of his story. Sandy reflects on his early career at Ingersoll Rand, where he and his co-founders began their entrepreneurial journey. They initially focused on research, helping top research organizations convert unstructured data into structured formats. However, they soon realised the challenges of scaling in that space, leading to their first pivot towards enterprise solutions.As the conversation unfolds, Sandy discusses the importance of recognising when to pivot and the necessity of being brutally honest with oneself about the business's direction. He recounts the pivotal moment when they decided to focus solely on healthcare, a notoriously difficult industry, and the challenges they faced during that transition. Sandy emphasises the significance of mutual respect and transparency among co-founders, which has been crucial in navigating the highs and lows of their journey and delve into the dynamics of the founding team, discussing how relationships evolve through challenges and the importance of having a strong support system. Sandy shares insights on recognizing personal limitations and the need for self-reflection, encouraging founders to be honest about their capabilities and to seek help when necessary.Sandy provides valuable lessons learned from his experiences, including the importance of long-term vision, the role of investors, and the necessity of adapting to industry changes, particularly with the rise of AI. He emphasizes that while the journey is fraught with challenges, enjoying the company of fellow founders and maintaining strong relationships can make the experience worthwhile.Join us for this insightful episode as we explore the rollercoaster ride of entrepreneurship, the importance of adaptability, and the value of camaraderie among founders.

Resources

Innovaccer Website

Innovaccer LinkedIn page

Sandy on Linkedin

MyStartUpCFO LinkedIn Page

MyStartUpCFO Website

Sandeep Shroff on Linkedin

Gaurav Rastogi on Linkedin

Chapters

00:00:00 - Introduction to the Rollercoaster Journey

00:01:13 - Meet the Hosts and Guest

00:02:22 - Sandy's Inception Story

00:03:00 - From Research to Enterprise

00:07:24 - The First Major Pivot to Healthcare

00:10:02 - Navigating the Healthcare Landscape

00:12:21 - Defining Success and Enjoying the Journey

00:13:10 - The Importance of Co-Founder Relationships

00:16:01 - Recognizing Personal Limits00:19:13 - The Role of Honesty in Leadership

00:20:10 - Co-Location and Communication Among Founders

00:21:06 - Rules for Healthy Disagreements

00:22:15 - Second-Guessing Decisions

00:24:39 - Investor Relationships and Long-Term Vision

00:27:49 - The Value of Trustworthy Investors

00:29:24 - Painful Lessons from Co-Founder Dynamics

00:32:07 - The Role of Luck in Co-Founder Relationships

00:33:10 - Rapid Fire Questions

00:38:11 - Conclusion and Final Thoughts#StratUpTherapy

In our latest episode, "Pivoting with Purpose," hosts Sandeep Shroff and Gaurav Rastogi sit down with Kabir Mathur, the co-founder of Leen, for a candid conversation about the art of the pivot – and why sometimes the best way forward is sideways! In this episode of our podcast, Sandeep Shroff, founder and CEO of My Startup CFO, delve into the often unspoken challenges faced by startup founders and entrepreneurs. Joined by Gaurav and our guest Kabir, the CEO and co-founder of Lean.dev, we explore the theme of "Pivoting with a Purpose."We kick off the discussion by acknowledging the critical importance of adaptability in the startup world. As Kabir shares his journey, we learn about his extensive experience in various sectors, including gaming, ad tech, B2B SaaS, and now cybersecurity. He introduces Lean.dev, a company focused on creating a unified API for security data, addressing the complexities of communication among the myriad of cybersecurity tools available today.Kabir recounts the initial phase of his entrepreneurial journey, where he and his co-founders aimed to develop a co-pilot for customer success teams, leveraging AI to enhance their efficiency. However, despite their enthusiasm and extensive customer discovery efforts, they faced significant challenges in gaining traction. The team conducted numerous outreach efforts, only to receive lukewarm responses and a lack of commitment from potential customers and investors.As the conversation unfolds, we discuss the pivotal moment when Kabir and his team realised that their original idea was not viable. They faced a harsh reality: while their concept resonated with many, it lacked the necessary market commitment. This led to a critical turning point where they had to confront the void left by abandoning their initial vision.Kabir emphasises the importance of having a strong team dynamic during this challenging period. He credits his co-founders, Neil and Akash, for their resilience and maturity, which helped them navigate the emotional turmoil of pivoting. The team engaged in a structured brainstorming process to generate new ideas, ultimately leading them to explore opportunities in the cybersecurity space.The episode highlights the significance of gathering and interpreting market signals, as Kabir shares their methodical approach to customer interviews and idea validation. Links:First Round ReviewThe Mom TestLenny's PodcastLeen's websiteLeen's LinkedIn pageMyStartUpCFO LinkedIn Page MyStartUpCFO WebsiteSandeep Shroff on LinkedinGaurav Rastogi on LinkedinKabir Mathur on Linkedin00:00:00 - Introduction to the Podcast and Theme of Pivoting00:01:00 - Introducing Kabir and His Background00:02:30 - Kabir's Journey in Startups00:04:30 - Initial Idea: Customer Success Co-Pilot00:08:00 - Realization of Failure and Need to Pivot00:10:30 - Customer Discovery Process00:12:30 - Challenges with Customer Commitment00:13:30 - Feedback from VCs and the Importance of Signals00:15:30 - Navigating Team Dynamics During Challenges00:18:00 - The Emotional Toll of Rejection00:20:00 - The Process of Idea Generation After Failure00:22:30 - Evaluating New Ideas with a Scientific Approach00:25:00 - Understanding the Cybersecurity Space00:27:00 - The Moment of Hitting the Wall00:30:00 - Processing Grief and Moving Forward00:32:00 - Finding a New Direction: The Cybersecurity Idea00:34:00 - Unexpected Commitment from Potential Customers00:45:00 - Conclusion and Reflections on the Journey

In this episode of #StartupTherapy Sandeep Shroff, CEO & Co-founder of myStartUpCFO and Gaurav Rastogi, Founder of DoLoop Digital, explore the mindset and strategies of entrepreneurs, focusing on resilience, energy management, and the importance of optimism in navigating the challenges of running a startup. They share personal experiences and insights on maintaining motivation and effectively leading a team through the ups and downs of the entrepreneurial journey. In this conversation, Debu Chatterjee, CEO, Konfer.ai, discusses various aspects of entrepreneurship, focusing on healthcare governance, team dynamics, the balance between optimism and pessimism, family involvement in startup life, and the importance of perseverance. He emphasizes the need for transparency within teams, understanding individual energy sources, and the challenges of navigating personal and professional life as a startup founder. Sandeep also critiques conventional wisdom in the startup world, advocating for a more flexible approach to strategic goals and hiring practices. Summary

• Entrepreneurs are inherently optimistic, which is crucial for success.
• A balance of optimism and a few pessimists in the team is beneficial.
• Resilience is key to surviving the unpredictable nature of startups.
• Sources of energy for founders include passion, drive, and team commitment.
• Setting long-term goals beyond financial gain is essential for motivation.
• Daily rituals like yoga and meditation can help maintain mental health.
• Signal attenuation occurs in organizations; find amplifiers to spread the passion.
• Pivots in business should be seen as learning opportunities, not failures.
• Effective delegation is crucial for team engagement and success.
• Maintaining high energy levels is vital for inspiring the team.
• Healthcare governance in generative technology is a promising area.
• Understanding team dynamics is crucial for sustained energy.
• Optimism is important, but a balance with realism is necessary.
• Family dynamics play a significant role in an entrepreneur's journey.
• Knowing when to pivot or abandon an idea is vital for success.
• Hiring practices should prioritize cultural fit over speed.
• Survival in the startup world often hinges on perseverance.
• Transparency within teams fosters a healthier work environment.
• The journey of entrepreneurship is filled with unpredictable challenges.
• Long-term strategic goals should be adaptable to changing circumstances.

Follow us: Sandeep Shroff Linkedin:   / sandeepshroff   Gaurav Rastogi Linkedin:   / gauravrastogi   Debu Chatterjee Linkedin:   / debuchatterjee   Chapters: 00:00:00 - The Optimistic Entrepreneur 00:01:08 - Introduction to Startup Therapy 00:01:42 - Resilience in Entrepreneurship 00:02:56 - Meet the Speakers: Gaurav and Debu 00:05:32 - The Startup Rollercoaster 00:07:51 - Sources of Energy for Founders 00:10:01 - The Importance of Optimism 00:12:00 - The Role of Pivots in Startups 00:15:43 - Translating Passion to Teams 00:20:03 - Signal Attenuation in Organizations 00:24:06 - The Balance of Optimism and Pessimism 00:29:08 - Family Engagement in the Startup Journey 00:34:08 - Perseverance vs. Walking Away 00:39:09 - Conventional Wisdom in Startups 00:42:14 - Hiring and Market Fit Challenges 00:45:09 - Learning from Mistakes 00:48:04 - Finding Energy and Resilience #StratUpTherapy