Not Another CEO Podcast

What happens when the company you built… is no longer yours?

Rob LoCascio, Founder of LivePerson, shares the full, unfiltered reality of building, scaling, losing, and rebuilding as a founder. From starting with almost nothing to taking his company public, scaling it from $900M to $4B in just 12 months during COVID and then facing the brutal reality of losing control of what he built.

In this conversation, Rob opens up about the hardest chapter of his career: fighting to hold onto his company, the emotional toll of watching it decline after his departure, and the moment he realized that everything he created was at risk.

He also dives into what separates founders who come back from those who don’t, why creativity is the one asset no one can ever take from you, and how to rebuild your identity when the company you built is no longer yours.

This isn’t just a story about success or failure it’s about ownership, resilience, and what it really means to be a builder.

If you’re building something or afraid of losing it this episode will hit hard.

Takeaways:

They Can Take the Company, Not the Builder: Rob’s biggest realization came after losing control everything external can be stripped away, but your ability to create, build, and execute is untouchable. That’s the real edge founders have.

Scaling Fast Comes With Hidden Risk: Going from $900M to $4B in 12 months sounds like a dream but hypergrowth brings pressure, expectations, and fragility that most people don’t see until it’s too late.

Founder Identity Is the Real Battle: Losing a company isn’t just financial it’s deeply personal. Rob breaks down what it feels like to lose something you poured your life into, and how to rebuild from that.

Fighting for What You Built Isn’t Optional: When things started slipping, Rob didn’t walk away he fought. And he explains why that fight was the hardest thing he’s ever faced as a leader.

Your Gift Is the Only Constant: Markets change, companies rise and fall but your creativity, vision, and ability to build are the only things that stay with you for life.

Quote of the Show:
"They can take your company. They can take your money. But they can’t take your creativity, the ability to build again." - Rob LoCascio

Links:
- LinkedIn: https://www.linkedin.com/in/rlocascio/
- LivePerson: https://www.liveperson.com
- KID Company: https://www.kidco.ai/
- Uare.ai: https://www.uare.ai/

Chapters:
00:00 – Intro
01:19 – From nothing: $5K, a couch, and starting over
02:10 – Building LivePerson and going public
05:30 – The COVID surge: $900M to $4B in 12 months
09:45 – When things started to break
14:20 – Losing control of the company he built
18:05 – The hardest fight of his career
22:40 – Watching the company decline after leaving
27:15 – The emotional toll of losing everything
31:50 – Identity beyond the company
36:10 – Why founders can always build again
41:25 – Creativity as the ultimate unfair advantage
46:00 – What Rob is building next
50:30 – The real meaning of success and failure

What really happens when you bet it all on your company & end up with nothing?

Ra'anan Cohen, Author & Founder of MobileMax and Bringg, pulls back the curtain on what most founders never talk about going from IPO to broke, rebuilding from zero, and finally selling at a $1 billion unicorn valuation with the scars to prove it.

In this conversation, he shares why he turned down $10M in stock at a public company and lived to regret it, how he secretly rebuilt himself while the whole industry thought he was already rich, and what changed at Bringg that made him finally know when to pull the plug.

If you're building something and trying to figure out when to hold and when to fold, this episode is for you.

Takeaways:

• Build the Team First, Everything Else Second: The single biggest factor in both MobileMax and Bringg was team. Ra'anan implemented a strict no-asshole policy at Bringg not just hiring for talent, but for personality, attitude, and the ability to endure a long, grinding journey.
• Know When to Take the Money: Turning down $10M in stock from institutional investors during MobileMax's IPO when the company was worth $100M cost Ra'anan everything. He walked away from Bringg at $1B because the 8-year scar from MobileMax kicked in.
• Fake It Till You Make It Has a Dark Side: After MobileMax collapsed, Ra'anan went to startup meetups while secretly broke and struggling watching everyone else perform success. He later learned everyone was doing the same thing. His book, Confessions of a Unicorn Founder, exists specifically to break this culture open.
• Secondary Is a Founder's Right, Not a Weakness: Old-school investors want founders "hungry." Ra'anan disagrees. Taking secondary closes the open loops in your brain the daily stress about going to zero and actually frees founders to dream bigger and swing harder, not less.

Quote of the Show:

"People like to say startup is like a roller coaster. I think this is very misleading. In the startup life as a founder, 90, 95% of the time I'm in crisis mode. It's not a roller coaster it's a marathon." - Ra'anan Cohen, Author & Founder of MobileMax & Bringg

Links:

• Book: Confessions of a Unicorn Founder - available on Amazon
• LinkedIn: https://www.linkedin.com/in/raananc/
• Website: www.raanancohen.com

Chapters:

00:00 – Intro: From IPO to zero to unicorn Ra'anan's full arc

01:22 – The one thing that had the biggest impact: team building

06:00 – The no-asshole policy and how to hire for attitude

08:50 – Framing hard weeks as progress the "great week" mantra

13:48 – MobileMax: the IPO, the $10M phone call, and saying no

16:32 – Why Ra'anan didn't sell a single stock and what it cost him

18:54 – When the iPhone reshaped mobile and MobileMax spiraled

25:05 – Broke and "the guy who made it" faking it at startup meetups

32:14 – The personal cost: family, presence, and the founder's obsession

34:13 – How a late pizza sparked the idea for Bringg

36:39 – Bringg's rise: customers, unicorn valuation, and pulling the plug

38:35 – Secondary, investor philosophies, and closing the open loop

45:26 – Fairness for founders: why secondary isn't just smart, it's right

50:15 – Writing Confessions of a Unicorn Founder and what comes next

52:02 – The one piece of advice Ra'anan would give his younger self

What if the reason your company isn’t growing… is because you’re spending too much time inside the company instead of with your customers?

Erica Jain, Co-Founder & CEO of Healthie, breaks down how a relentless customer-first mindset shaped every part of the business from product decisions to hiring to long-term strategy.

In this conversation, she shares how they got their first customers with no sales experience, why internal inefficiency is a bigger risk than doing too much, and what it really takes to maintain speed as a company scales. She also dives into rebuilding the product after early success, hiring for values, and staying in control while growing a profitable company.

If you want to build faster, stay close to your customers, and avoid the trap of internal complexity slowing you down this episode is for you.

Takeaways:

• Obsess Over Customers as Your True North Star: The single most important thing is to instill a true customer-first mindset across the entire company. Customers literally “keep our lights on” every decision, roadmap, and internal process should revolve around delivering an incredible experience for them.
• Simplify Your Values Ruthlessly: Erica and her team reduced their values from eight which nobody could remember to just the Three R’s: Respect, Resilience, and Reliability. Hire for values far more than skills, especially as technology changes rapidly.
• Profitability Equals Control: They chose to remain profitable for most of the company’s life to always stay in control of their destiny. Build a generational business and raise capital only when it serves clear long-term goals, never out of desperation.
• Mediocrity Is the Real Killer: Companies don’t usually die from doing too many things they die from descending into mediocrity caused by slow internal processes, too many meetings, and inefficient decision-making. Speed and execution velocity matter enormously.
• Hiring, Team Building, and Scaling Challenges: Hiring for values, the difficulty of identifying customer-first people in interviews, retaining talent (many team members 5–7+ years), going through a major codebase rewrite, and the constant battle against internal inefficiency as the company grows.

Quote of the Show:

• The one thing I would do is instill… a true customer first mindset. There is something incredibly, incredibly powerful about waking up every single minute of every single day and wholeheartedly focusing on making sure our customers are taken care of.”- Erica Jane, CEO & Co-Founder of Healthie.
  

Links:

• LinkedIn: https://www.linkedin.com/in/ericajain/
• Website: https://www.gethealthie.com/

Chapters

00:00 – Intro: Healthie’s growth, impact & profitability

00:56 – The power of a true customer-first mindset

03:11 – How to build with customers from day one

06:00 – Hiring for values: the “3 R’s” framework

08:53 – Evolving culture as the company scales

12:54 – Operating systems & using OKRs effectively

16:50 – Why inefficiency kills companies (not ambition)

19:35 – Profitability, fundraising & staying in control

24:08 – Starting Healthie & getting first customers

30:30 – Biggest challenges: tech debt & rebuilding the product

How can one simple strategy drive your company’s success? In this solo episode of Not Another CEO Podcast, host David Politis dives deep into the significance of alignment and prioritization within a company. Reflecting on a personal article shared via Substack, David emphasizes the importance of refocusing and reprioritizing company goals as new challenges and opportunities arise.

Takeaways: 

• Concentration of Efforts: Narrowing down the focus to one primary goal can unify and effectively drive a company's momentum. By concentrating efforts, every team member can contribute to company growth.
• Effective Communication: Regular and focused communication is key to keeping everyone aligned with the company's goals. David suggests updating the team weekly to maintain a cadence that ensures urgency and focus.
• Culture of Outcome-Based Work: Create a work culture that rewards achievements based on outcomes rather than just effort. It’s crucial for employees to understand their work's impact on the company's success.
• Celebration of Successes: Recognizing and celebrating achievements fosters a positive work environment and encourages further productivity. Celebrations can be as simple as an email recognition or a shoutout during all-hands meetings.
• Strategic Compensation: Implementing flexible compensation structures isn't limited to sales teams. Properly aligning compensation with company goals can motivate teams across the board to go above and beyond.
• Removing Distractions: Encourage leadership to stay concentrated on key goals by avoiding changes in priorities throughout the quarter. Written notes can capture evolving ideas, which can then be revisited during the next planning phase.
• Leadership Involvement: Leaders should actively remove barriers for their teams rather than changing priorities. This approach helps maintain focus and supports execution on high-priority initiatives.

Quote of the Show:

• “The less you communicate about the other things, and the more you just make all the communication about that thing, people are gonna understand this is what we're focusing on." - David Politis

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #MarchPulse

Chapters:

00:00 Intro

00:48 Q2 Reprioritization Problem

02:36 Five Cs Framework

02:47 Concentrate Efforts

04:32 Communicate With Cadence

05:55 Outcome Driven Culture

06:44 Celebrate The Wins

08:13 Compensation Drives Behavior

11:26 Stay Focused For A Quarter

12:49 Outro

What does it take to transform a struggling startup into a booming enterprise? In this episode of Not Another CEO Podcast, host David Politis sits down with Didi Gurfinkel, Co-Founder and CEO of Datarails. Together, they delve into Didi's decade-long journey of building a successful financial platform from scratch, discussing both the struggles and triumphs of his entrepreneurial path.

From his early days at Cisco to co-founding Datarails, Didi shares invaluable lessons on startup pivoting, embracing new technologies, and harnessing AI to revolutionize financial operations.

Takeaways: 

• The Power of the Right Team: Didi highlights the importance of having the right co-founders. He credits the success of Datarails largely to the strong foundational team that shared common goals and complementary skills.
• Embracing the Brutal Truth: Didi emphasizes the need for leaders to be honest about their failures and to learn from them while maintaining a visionary outlook for the future.
• Importance of Having a Name: Drawing from past experiences, Didi advises startups to choose a product that has a recognisable name and existing budget line.
• Finding Your Ideal Market Fit: Datarails achieved success by narrowing their focus to finance professionals who love Excel, aligning product benefits with users’ existing skills and preferences.
• Strategic Use of AI: Datarails seeks to prepare organizations for AI integration, ensuring readiness for technological advancements.
• Balancing Work and Family: Didi points out that while entrepreneurship is all-consuming, showcasing the possibility of building something significant can offer invaluable lessons for family.

Quote of the Show:

• “If someone ask me, I'm not sure if I have the product market fit, I'm saying, no, you don't have it. If you had it, you know." - Didi Gurfinkel

Links:

• LinkedIn:https://www.linkedin.com/in/didigurfinkel/ 
• Website: https://www.datarails.com/   
  

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify:https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

Chapters:

00:00 Intro

01:21 Co-Founders Matter Most

02:28 Finding the Right Partners

05:47 Evolving Founder Roles

07:28 Five Tough Early Years

09:28 Building Tech Without Sales

13:08 Staying Motivated to Pivot

18:05 The Breakthrough Pivot

20:52 Why FP&A and Mid-Market

24:40 Scrappy Early Go-To-Market

26:38 LinkedIn Phone Number Hack

28:17 Knowing Product Market Fit

30:43 Removing Buying Friction

32:47 Zero to One Million ARR

35:26 AI and Finance OS Vision

41:38 Three Year Company Outlook

43:06 Founder Origin Story

46:25 Israel Startup Mindset

47:50 No Work Life Balance

51:02 Outro

What sets apart the founders who persevere through immense challenges and come out stronger on the other side? In this episode, David sits down with Shaun Abrahamson, Co-Founder & Managing Partner at Third Sphere. Shaun shares his unique insights into the high-stakes world of venture investing, particularly in climate tech and hardware, reflecting on the kinds of founders he backs and the unforeseen hurdles they've had to overcome.

Shaun delves into his philosophy on investing in early-stage companies, emphasizing the importance of resilience and adaptability in founders. He also discusses the intricacies of climate tech investment and the lessons he's learned from over two decades in the field. 

Takeaways:

• The Importance of "Burned Bridges": Shaun explains that he looks for founders who feel they have no option but to succeed, drawing a comparison to immigrants or those without a fallback, which can drive relentless focus and fortitude.
• Signals of Early-Stage Investment: Investing at the pre-seed stage involves identifying teams with potential through their work product rather than initial conversations. 
• Challenges of Climate Tech Investing: The difficulty in obtaining clear customer signals within climate tech is highlighted. Shaun notes that genuine customer commitment is hard to gauge and is essential for moving beyond pilot projects.
• Weathering the Storms: Shaun emphasizes that founders who persist through geopolitical challenges, like supply chain disruptions and tariffs, emerge uniquely stronger. 

Quote of the Show:

• “Portfolio math is brutal because it basically says that most companies don’t matter… it’s very easy to say, it’s very hard for founders to accept they may not be that one or two companies." - Shaun Abrahamson

Links:

• LinkedIn: https://www.linkedin.com/in/shaunabe/ 
• Website: https://thirdsphere.com/ 
  

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify:https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts:https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube:https://www.youtube.com/@NotAnotherCEOPodcast 

Chapters:

00:00 Intro

01:30 Burned Bridges Mindset

03:47 Early Bets And Bad Logos

06:20 YC Founder Signal Noise

08:48 Work Product Over Pitch

11:32 Climate Hardware Realities

15:39 Lego Building To Revenue

17:29 Tariffs And Supply Chain Chaos

20:02 Founders Forged By Turmoil

23:54 Why Third Sphere Went Climate

26:29 Mission Driven Founder Support

27:26 Belief And Reality Checks

30:41 Direct Feedback As A VC

35:35 Private Credit Replaces Banks

39:15 Founder Updates And Trust

44:29 Portfolio Math Harsh Truths

49:09 Biggest Missed Deal

50:46 Next Decade Climate Bets

53:16 Outro

What makes a startup truly successful in the eyes of venture capitalists? In this episode of Not Another CEO Podcast, host David Politis sits down with Rudina Seseri, Founder and Managing Partner at Glasswing Ventures, to dive into the realm of venture capital and discuss how startup founders can better position themselves for success.

From her experience with early-stage companies to her unique perspective on the dynamics of venture capital, Rudina shares invaluable lessons about the importance of execution, understanding investor expectations, and the intricacies of navigating the startup ecosystem.

Takeaways: 

• The Value of Execution: For Rudina, the key trait she seeks in founders is execution excellence. It's not just about having a vision but demonstrating the ability and hustle to deliver beyond expectations.
• The Misunderstood VC Role: Many founders and employees don't understand the source of venture capital. Knowing that VCs manage funds from institutions like endowments and pensions changes the stakes and expectations.
• Importance of Strategic Partnerships: Rudina advises founders to seek investment from firms and partners that align with their stage and needs, rather than solely pursuing big names which might not provide necessary support.
• The Art of Quick Decision-Making: Efficiency in decision-making during early meetings can shape successful partnerships. Rudina values honesty in communicating why a VC might pass on an opportunity, emphasizing that a quick, thoughtful no is better than indecision.
• Sustained Support Post-Investment: At Glasswing Ventures, support continues beyond just funding, emphasizing talent acquisition, customer connections, and strategic guidance, ensuring startups grow sustainably.

Quote of the Show:

• “What have we done for them lately to deserve to expect? Yes we’ve provided capital, but that’s not enough in my book." - Rudina Seseri

Links:

• LinkedIn:https://www.linkedin.com/in/rudinaseseri/   
• Website: https://glasswing.vc/  

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify:https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts:https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube:https://www.youtube.com/@NotAnotherCEOPodcast 
  

Chapters:

00:00 Intro

01:37 Ruthless Execution

02:32 Spotting Hustle Fast

05:38 Execution in the AI Boom

07:55 Retention and Switching Costs

10:08 AI Interest vs Intent

13:19 AI Hype and Human Loop

17:58 How VCs Decide Quickly

20:39 Giving Fast Honest Nos

22:54 Execution and Go To Market Gaps

24:21 How VCs Support Founders

27:14 Portfolio Review Cadence

28:27 Why Take Board Seats

33:30 Term Sheets Beyond Valuation

38:17 Choosing Firm vs Partner

41:29 Scaling Support With Team

43:01 Why She Became an Investor

45:14 Outro

How do you choose an investor you’ll still trust when things inevitably get hard?

In this episode, Ian Sigalow offers a candid, unfiltered look at early-stage investing and the founder–investor relationship, including one of the most sobering truths first-time founders often learn too late: it’s far harder to unwind a bad investor than a bad marriage. Drawing from decades of experience backing companies and founders at Greycroft, Ian breaks down how great investors actually think, decide, and engage behind the scenes.

Ian shares what he looks for in exceptional founders, why the explosion of startups hasn’t increased the number of true breakout winners, and why most board meetings fail to create real value. This episode is a must-listen for any CEO navigating fundraising or building their first long-term investor relationships.

Takeaways: 

• Master of Two Domains: Sigalow emphasizes the importance of founders who excel in both product understanding and sales, calling them "masters of two domains" who are rare and invaluable.
• Big Market Potentials: Ian points out the essential need for startups to target significantly large markets. In the entrepreneurial world, having the potential to scale a company to a billion-dollar business is vital.
• The Earned Secret: A distinctive aspect investors look for is the "earned secret."
• The Importance of Trust in Investor Relationships: Sigalow stresses that founders should only take money from investors they trust, highlighting the lasting nature of these partnerships. 
• Controlling the Board Meeting: Effective CEOs maintain control over board meetings, ensuring the focus remains on strategic issues rather than getting sidetracked. 

Quote of the Show:

• “A CEO should never take money from someone they don’t trust. It’s harder to get out of a bad investor than a bad marriage." - Ian Sigalow
  

Links:

• LinkedIn: https://www.linkedin.com/in/iansigalow/ 
• Website: https://www.greycroft.com/ 
  

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify:https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts:https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube:https://www.youtube.com/@NotAnotherCEOPodcast 
  

Chapters:

00:00 Intro

01:32 Founder's Qualities and Market Potential

03:01 The Importance of Earned Secrets

03:57 Challenges in Identifying Exceptional Founders

06:12 The Evolution of Venture Capital

17:42 The Role of Technology in Venture Capital

21:45 Focus on Early-Stage AI Investments

26:40 Choosing the Right Investment Partner

10:50 Onboarding Process at Greycroft

27:50 The Rule of Three in Communication

29:24 Key Metrics for Founders

31:21 The Role of Board Meetings

38:26 Understanding Venture Capital Dynamics

18:46 Ian's Journey into Venture Capital

48:04 Outro

How do you lead at scale when the role constantly asks you to stretch past what feels possible?

In this episode, Irina Novoselsky shares the honest, vulnerable truth behind leading at the highest levels: the job isn’t about having every answer, it’s about choosing to step into roles, decisions, and moments that stretch you and reveal what you’re capable of. Irina brings deep experience from modernizing CareerBuilder and now leading Hootsuite, the world’s most widely used social media management platform trusted by millions of users.

Irina walks through the systems, disciplines, and mindsets that have shaped her career, from the 15-minute weekly all-hands that transformed Hootsuite’s culture, to her 100-day onboarding playbook, to redefining the company’s ICP in 10 days and doubling growth. She also breaks down how Gen Z will reshape every company’s go-to-market motion, why naivete is an early-career superpower, and how her immigrant upbringing forged the resilience she leads with today.

Takeaways: 

• Embrace Focus and Prioritization: Irina emphasizes the addictive nature of focus and its role in driving growth. By identifying core strengths and doubling down on them, businesses can achieve unparalleled success.
• Redefine Company Rituals: Hootsuite’s unique weekly 15-minute all-hands meeting, serves as a crucial touchpoint. It's a tightly produced session that keeps the team energized and informed.
• Foster Transparency and Engagement: For Irina, transparency is key. She advocates for open communication and regular Q&A sessions, encouraging feedback, even the uncomfortable truths.

Quote of the Show:

• “I get scared frequently. I put myself in vulnerable moments all the time… but those are the moments when you realize you can do hard things." - Irina Novoselsky

Links:

• LinkedIn: https://www.linkedin.com/in/irina-novoselsky/ 
• Website: https://www.hootsuite.com/ 
  

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify:https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts:https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube:https://www.youtube.com/@NotAnotherCEOPodcast 

Chapters:

00:00 Intro

01:10 Irina's Leadership Style and Hootsuite's All Hands Meetings

06:53 The Importance of Transparency and Feedback

08:49 First Steps as a New CEO

14:27 Identifying Key Players and Cultural Carriers

18:14 The Power of Focus and Prioritization

23:53 Communicating with Investors and Board Members

26:35 The Role of Social Media and Personal Branding

28:42 Creating a Resonant Culture

29:20 The Power of Social Media for CEOs

30:31 Understanding Gen Z's Buying Behavior

33:15 Challenges and Growth as a CEO

36:18 The Importance of Vulnerability and Mentorship

51:17 Transitioning from Finance to Operations

54:03 Final Reflections and Advice

59:04 Outro

Can experience truly make a difference in the startup world? In this episode of Not Another CEO Podcast, David Politis speaks with Vanja Josifovski, Co-Founder and CEO of Kumo, to explore the journey of leading a cutting-edge AI enterprise. 

From his prestigious roles at Pinterest and Airbnb to founding Kumo, Vanja shares the lessons learned, the dilemmas faced, and the excitement of turning vast amounts of relational business data into actionable predictions.

Takeaways: 

• The Importance of Co-founders: Vanja emphasizes the critical role of choosing the right co-founders. He stresses the importance of complementary skills and experiences that create a sustainable and successful leadership team.
• Understanding Market Adaptability: A major challenge for technical founders can be the transition to understanding the go-to-market strategies. Vanja shares the struggles of innovating while aligning with market needs and effectively communicating product value.
• The Journey From Idea to Reality: Vanja sheds light on how Kumo's idea sprouted from a simple yet groundbreaking aspiration to simplify the process of turning enterprise data into predictions without the complex machine learning cycle.
• Raising Capital in the Current Climate: Although initially easy due to Vanja's background, he warns about the “honeymoon phase” in fundraising and the necessity of making money quickly, even when resources are abundant.
• The Art of Unlearning: As Vanja continues his journey, he highlights unlearning as key to adapting to new challenges. The ability to let go of old practices and adopt new methodologies is vital for growth and evolution.

Quote of the Show:

• “It’s always easier to watch somebody do things and criticize… if somebody’s watching you from the side, they’ll always find something wrong." - Vanja Josifovski

Links:

• LinkedIn: https://www.linkedin.com/in/vjosifovski/  
• Website: https://kumo.ai/ 

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
  

Chapters:

00:00 Intro

01:24 The Importance of Choosing the Right Co-Founders

04:44 Defining Roles Among Co-Founders

06:49 Challenges of Being a CEO

10:22 Hiring and Building a Team

12:54 Raising Capital and Investor Relations

15:21 Kumo's Product and Market Fit

18:57 Pricing Models and Strategies

24:28 Acquiring the First Customers

28:28 The Intensity of Starting a Company at 50

32:33 The Importance of Unlearning as a CEO

37:13 Challenges in Go-to-Market and Fundraising

39:14 Kumo's Vision for the Future

42:28 From Macedonia to Silicon Valley

52:54 Advice to My Younger Self

53:39 Outro