The VC Architects

Pablo Casilimas, co-founder and managing partner of One Six One Ventures, joins Vlad Cazacu, co-founder and CEO of Flowlie, to discuss his unconventional journey from an engineering student, through content marketing and event organizing, to founding 161 Ventures alongside a close friend. We cover strategies for sourcing and funding startups, the significance of founder-market fit, and insights into maintaining a venture fund's integrity by wisely managing GP entity ownership.
 

00:00 Welcome to VC Architects: Unveiling the Blueprint of 161 Ventures

01:06 The Genesis of 161 Ventures: From Engineering to Entrepreneurship

01:56 The Evolution of Gainesville's Startup Ecosystem

03:19 Pivoting from Engineering to Content Marketing: A Founder's Journey

06:32 Leveraging Events for Growth and Networking

09:06 The Birth of 161 Ventures: From Accelerator to Venture Fund

11:49 Securing the First Investors: Turning Vision into Reality

17:29 Navigating the Venture Fund Landscape: Insights and Strategies

20:36 The Art of Attracting Dual-Use GovTech Startups

21:55 Decoding Success in Enterprise Tech and GovTech

28:09 Lessons Learned and the Path Forward for Emerging Fund Managers

41:35 Gratitude and Reflections: The People Behind the Journey

You can find Pablo Casilimas on LinkedIn at https://www.linkedin.com/in/pablo-casilimas-1707a9113/ and on Twitter at https://twitter.com/pablo_casilimas and learn more about OneSixOne Ventures at https://www.onesixone.ventures/.

Learn more about Flowlie and how the platform can help you screen deals faster and discover the right connections from your network at https://www.flowlie.com.

Stay up-to-date with all our episodes by checking our website at https://www.thevcarchitects.com, following us on Twitter at https://twitter.com/thevcarchitects, and on Instagram at https://www.instagram.com/thevcarchitects.

Genevieve LeMarchal, co-founder and managing partner of Suncoast Ventures, joins Vlad Cazacu, co-founder and CEO of Flowlie, to discuss her journey from management consultant turned sales trainer to startup acceleration, healthcare tech, and VC fund manager. We discuss her passion for assisting entrepreneurs, her confrontation with imposter syndrome, and the origins of Suncoast Ventures. The conversation touches upon Genevieve's significant relationship-building efforts within her ventures and the importance of providing differentiated value to founders.
 

00:01 Introduction and Welcome

01:21 The Journey to Venture Capital

05:29 Learning from Failures

07:51 The Challenges of Fundraising

08:43 Transitioning to the Investor Side

14:42 The Genesis of Suncoast Ventures

18:21 The First Steps in Venture Capital

22:46 The Journey to Launching Cohorts and Accelerators

24:13 Overcoming Imposter Syndrome and Embracing Opportunities

25:03 The Struggle with Self-Doubt and Building Confidence

27:35 The Role of VC Lab in the Journey

31:17 The Vision for Suncoast Ventures

36:44 The Inception of Suncoast Ventures

38:19 Building a Diverse Team and Ecosystem

39:41 The Value-Driven Approach to Investing

45:37 Gratitude and Reflections

46:49 Closing Remarks and Future Prospects

You can find Genevieve LeMarchal on LinkedIn at https://www.linkedin.com/in/genevievelemarchal/ and on Twitter at https://twitter.com/genlemarchal and learn more about Suncoast Ventures at https://www.suncoastvc.com/.

Learn more about Flowlie and how the platform can help you screen deals faster and discover the right connections from your network at https://www.flowlie.com.

Stay up-to-date with all our episodes by checking our website at https://www.thevcarchitects.com, following us on Twitter at https://twitter.com/thevcarchitects, and on Instagram at https://www.instagram.com/thevcarchitects.

Jahn Karsybaev, co-founder and managing partner of Big Sky Capital, joins Vlad Cazacu, co-founder and CEO of Flowlie, to discuss his journey from a multi-time entrepreneur to an angel investor and now fund manager. We unpack insights on fundraising for first-time fund managers, and the role of relationship-building in securing fruitful partnerships with LPs. John emphasizes the importance of maintaining a long-term vision, cultivating reputation and credibility, and bringing value to portfolio companies.

00:00 Introduction and Background of the Hosts

00:17 The VC Architects Podcast: An Overview

00:56 Sponsorship Message

01:07 Beginning of the Interview with Jahn Karsybaev

01:32 Jahn's Journey Before Angel Investing

04:00 Jahn's Entrepreneurial Journey and Lessons Learned

07:55 The Investment Thesis of Big Sky Capital

10:27 The Process of Discovering Upcoming Entrepreneurs

14:36 The Importance of Building Relationships in Venture Capital

14:50 The Fundraising Journey for Big Sky Capital

17:20 The Vision for Big Sky Capital

31:21 Mistakes and Lessons Learned During Fundraising

39:01 Looking Forward: The Future of Big Sky Capital

42:07 Rapid Fire Questions and Conclusion

You can find Jahn Karsybaev on LinkedIn at https://www.linkedin.com/in/jahnibek/ and on Twitter at https://twitter.com/jahnibek_ and learn more about Big Sky Capital at https://bigskycapital.co/.

Learn more about Flowlie and how the platform can help you screen deals faster and discover the right connections from your network at https://www.flowlie.com.

Stay up-to-date with all our episodes by checking our website at https://www.thevcarchitects.com, following us on Twitter at https://twitter.com/thevcarchitects, and on Instagram at https://www.instagram.com/thevcarchitects.

Luke Cooper, founder and managing partner of Latimer Ventures, joins Vlad Cazacu, co-founder and CEO of Flowlie, to discuss his journey from M&A lawyer to multi-time exited entrepreneur turned venture investor. He opens up about the pain, profit, and purpose that drove his transition and the impact he hopes to make as an investor. Luke also dives into his thesis at Latimer Ventures, which focuses on supporting black and Hispanic founders in the US.

You can find Luke Cooper on LinkedIn at https://www.linkedin.com/in/lukecooperbaltimore/ and learn more about Latimer Ventures at https://www.latimer.vc/.

Learn more about Flowlie and how the platform can help you screen deals faster and discover the right connections from your network at https://www.flowlie.com.

Stay up-to-date with all our episodes by checking our website at https://www.thevcarchitects.com, following us on Twitter at https://twitter.com/thevcarchitects, and on Instagram at https://www.instagram.com/thevcarchitects.

Paige Doherty, co-founder and managing partner of Behind Genius Ventures, joins Vlad Cazacu, co-founder and CEO of Flowlie, to discuss her journey from student of the venture ecosystem to the youngest-ever fund GP. In this episode, we unpack Paige's content creation strategy, the early syndication days, and the first LP check.

You can find Paige Doherty on X at https://twitter.com/paigefinnn and learn more about Behind Genius Ventures at https://www.behindgeniusventures.com/.

Learn more about Flowlie and how the platform can help you screen deals faster and discover the right connections from your network at https://www.flowlie.com.

Stay up-to-date with all our episodes by checking our website at https://www.thevcarchitects.com, following us on Twitter at https://twitter.com/thevcarchitects, and on Instagram at https://www.instagram.com/thevcarchitects.

Ivan Montoya, founder and managing partner of NuMundo Ventures, joins Vlad Cazacu, co-founder and CEO of Flowlie, to discuss the SF Bay as it was in the late 90s, his journey to becoming LATAM's super angel and the decision to start his own fund.

You can find Ivan Montoya on LinkedIn at https://www.linkedin.com/in/ivanmontoya1/ and learn more about NuMundo Ventures at https://numundoventures.com/.

Learn more about Flowlie and how the platform can help you screen deals faster and discover the right connections from your network at https://www.flowlie.com.

Stay up-to-date with all our episodes by checking our website at https://www.thevcarchitects.com, following us on Twitter at https://twitter.com/thevcarchitects, and on Instagram at https://www.instagram.com/thevcarchitects.

Maxine Minter, founder and managing partner of Co Ventures, joins Vlad Cazacu, co-founder and CEO of Flowlie, to discuss the Australian-US arbitrage opportunity, lessons from building her first fund, and the unusual VC market of '21 and '22.

You can find Maxine Minter on Twitter at https://twitter.com/minmintymin and learn more about CoVentures at https://www.coventures.vc/.

Learn more about Flowlie and how the platform can help you screen deals faster and discover the right connections from your network at https://www.flowlie.com.
 

Stay up-to-date with all our episodes by checking our website at https://www.thevcarchitects.com, following us on Twitter at https://twitter.com/thevcarchitects, and on Instagram at https://www.instagram.com/thevcarchitects.

Ihar Mahaniok, founder and managing partner of Geek Ventures, joins Vlad Cazacu, co-founder and CEO of Flowlie, to discuss the launch of his Fund I and share some of the learnings acquired as one of the most active angel investors in immigrant founders.

You can find Ihar Mahaniok on Twitter at https://twitter.com/mahaniok and learn more about Geek Ventures at https://geek-ventures.com/.

Learn more about Flowlie and how the platform can help you screen deals faster and discover the right connections from your network at https://www.flowlie.com.

Stay up-to-date with all our episodes by checking our website at https://www.thevcarchitects.com, following us on Twitter at https://twitter.com/thevcarchitects, and on Instagram at https://www.instagram.com/thevcarchitects.

From J.P.'s reflections on inefficiencies in the supply chain to his passion for groundbreaking technologies, discover the secrets that drive the next generation of supply chain innovations. Don't miss out on Keating's insights into the importance of diversity in the industry, his valuable lessons from several CVC firms, and a special segment where he pays tribute to a mentor who shaped his journey. Tune in for an episode filled with wisdom, revelations, and a sprinkle of humor!

1. [00:00:00] JP Keating introduces himself as the managing partner and founder of ProChain Ventures, emphasizing their mission to invest in next-gen supply chain technologies. Vlad Cazacu introduces the podcast, "The VC Architects," and highlights Keating's extensive experience in supply chain and procurement.
2. [00:01:00] The episode's sponsor, Flowlie, is introduced as the top choice for deal screening and network management. Vlad welcomes JP and expresses appreciation for his participation.
3. [00:02:00] JP Keating discusses his wide-ranging experiences across different industries and Fortune 500 companies. He speaks about his constant curiosity and the drive to learn and explore various facets of businesses.
4. [00:03:00] JP reflects on his career, contemplating different roles he could take on a global scale. He shares his passion for innovation and how his journey led him to the world of venture capital, especially during the rise of accelerators.
5. [00:04:00] Keating expresses his frustrations with the inefficiencies, waste, and poor working conditions prevalent in many enterprises. He laments the lack of transparency and data understanding in supply chains.
6. [00:05:00] Keating elaborates on his passion for fixing broken supply chains. He emphasizes the urgency to address both technological and societal challenges within the supply chain industry. The goal is not just to address the physical and financial issues but also to rectify societal problems.
7. [00:06:00] The conversation shifts to the importance of values and intentions in the venture space. Vlad Cazacu compares Keating's journey to that of a founder, highlighting the challenges and decisions faced.
8. [00:07:00] JP reminisces about his time around Boeing Ventures and its evolution. He shares insights into the early stages of corporate ventures and the challenges faced in fostering innovation within large corporations.
9. [00:08:00] Keating discusses his role in leading corporate-startup collaboration, especially during his tenure at utilities. He emphasizes the importance of supplier diversity programs, highlighting the potential for collaboration with small businesses, minority-owned entities, and other specialized groups.
10. [00:09:00] At ConAgra, JP encountered a surge in food innovation and AgTech. He details his efforts to establish a corporate venture initiative to invest in early brands, ingredients, and materials. Additionally, he reflects on the significant contributions of minorities and women in launching new food and beverage brands, advocating for a more inclusive approach.
11. [00:10:00] JP Keating discusses his ambition to create an external innovation program through the supply chain group, with a vision of making it the most innovative entity within the enterprise. He emphasizes collaboration with corporate ventures and development teams to drive innovation.
12. [00:11:00] Sharing his journey, Keating talks about the desire to create something of his own alongside partners who share the same mission. He expresses his appreciation for corporate venture, emphasizing the importance of co-investing and the role of big enterprises as customers for portfolio companies.
13. [00:12:00] The conversation touches upon the momentum Keating experienced in his career, leading him to fully embrace the venture space. He describes the excitement and challenges of the venture journey.
14. [00:13:00] Keating delves into the specifics of ProChain Ventures, highlighting their focus on supply chain tech, both software and hardware, at the pre-seed and seed stages. He gives insight into their investment criteria, targeting valuations under $15 million and initial investments ranging from $100,000 to $250,000.
15. [00:14:00] Continuing the discussion on ProChain's investment strategy, Keating mentions their flexibility in ownership percentages. They prioritize being a part of promising ventures, even if it means having a smaller ownership stake. He further simplifies their focus on supply chain technology for better understanding.
16. [00:15:00] Keating discusses ProChain Ventures' investment in a first-mile company and emphasizes their commitment to working with diverse founders. He highlights their focus on companies that significantly impact decarbonization and sustainability, rather than directly investing in sustainability-specific firms.
17. [00:16:00] Building on the theme of sustainability, JP notes the significant role of supply chain operations in global emissions. He advocates for efficiency improvements, alternative fuels, innovative transportation methods, and advanced predictive technology to reduce waste and resource consumption.
18. [00:17:00] Vlad Cazacu inquires about the composition of Limited Partners (LPs) supporting ProChain Ventures.
19. [00:18:00] Keating describes their unique investor appeal, emphasizing their holistic approach. While they project strong financial returns, their primary focus is on achieving broader societal impacts, such as cost reductions and enhanced transparency for their portfolio companies' customers.
20. [00:19:00] JP provides insights into ProChain's investment strategy, pointing out that they typically target companies poised for acquisition rather than IPOs. He explains the return profiles attractive to their investors and touches upon the importance of synergy across their portfolio companies.
21. [00:20:00] Keating describes ProChain Ventures' investment expectations. While they have companies on the unicorn trajectory, their primary focus is on helping them establish solid businesses that generate cash flow and are acquisition targets within a reasonable timeframe.
22. [00:21:00] Discussing the investment approach, Vlad Cazacu inquires if the focus on acquisition at smaller multiples was a co-development with LPs or Keating's lead. Keating clarifies that he led with this strategy and the accepting LPs favored it. He emphasizes his preference for investing in foundational technologies ("picks and shovels") over consumer-facing brands.
23. [00:22:00] JP discusses the challenges of scaling consumer brands and the high costs involved. He contrasts this with the more stable, albeit less glamorous, supply chain companies that underpin society, which became evident during the COVID-19 pandemic.
24. [00:23:00] Keating delves into the endless innovation opportunities within the supply chain sector. He emphasizes the urgency of adopting technology to address labor shortages and the necessity of such technology for businesses to remain competitive, especially in the context of reshoring initiatives.
25. [00:24:00] Reflecting on ProChain Ventures' success with LPs, Keating credits the team's vast experience across multiple Fortune 500 companies. He differentiates their focus from firms that concentrate only on last-mile delivery, emphasizing the broader view they take on the entire supply chain system.
26. [00:25:00] Vlad Cazacu acknowledges the favorable trends that Keating and ProChain Ventures have tapped into. He begins to inquire about the kind of individuals who have been involved in their journey.
27. [00:26:00] JP Keating shares his initial intent to involve supply chain professionals as investors, primarily those capable of making smaller investments. However, he realized that many of them lacked a comprehensive understanding of venture capital and were hesitant about the risks involved.
28. [00:27:00] Despite the challenges of engaging traditional supply chain professionals as investors, Keating emphasizes the importance of volume in deal discovery. He notes the difficulty in identifying the right people who would resonate with their vision, given the vast number of potential deals.
29. [00:28:00] Keating recounts reconnecting with long-lost contacts who, despite the time gap, showed interest in investing in ProChain Ventures' deals. He emphasizes the significance of relationships and the trust established over time.
30. [00:29:00] Reflecting on their investor base, Keating acknowledges the challenges of attracting institutional investors at their current stage. He mentions the potential of such partnerships in future fund iterations. He also humorously wishes for a psychology degree and better sales skills to navigate the complexities of fundraising.
31. [00:30:00] Keating talks about a former colleague and boss who played a significant role in his journey. The trust and belief of this individual gave Keating confidence in his venture.
32. [00:31:00] Discussion on the timing of launching ProChain Ventures and the challenges and uncertainties of global events affecting investment strategies.
33. [00:32:00] The dedication to portfolio companies is highlighted. Keating speaks about the motivation and commitment he feels toward the founders he invests in.
34. [00:40:00] Keating reflects on the various individuals who've influenced him over the years, both famous figures like Richard Branson and everyday workers.
35. [00:41:00] The episode winds down with a gratitude segment where guests are asked to express gratitude to one person who's impacted their journey.
36. [00:42:00] JP chooses a significant mentor from his professional life and highlights his resilience and leadership.
37. [00:43:00] The podcast episode concludes, thanking listeners and giving a nod to the sponsor, Flowlie.

You can find J.P. Keating on LinkedIn at https://www.linkedin.com/in/jp-keating/ and learn more about ProChain Ventures at https://www.prochain.vc/.

Learn more about Flowlie and how the platform can help you screen deals faster and discover the right connections from your network at https://www.flowlie.com.

Stay up-to-date with all our episodes by checking our website at https://www.thevcarchitects.com, following us on Twitter at https://twitter.com/thevcarchitects, and on Instagram at https://www.instagram.com/thevcarchitects.

From his daring investment in Palantir during the 2009 financial crisis to the challenges of managing larger seed rounds in today's market, Sandy shares invaluable insights that every aspiring investor should hear. Stay tuned for some rapid-fire questions revealing a surprise interaction with Elon Musk, and discover why trust is the cornerstone of fundraising. Don't miss this riveting conversation!

1. Introduction and Overview [00:00:00]: Introduction of Sandy Kory and his background in VC. Overview of the podcast episode.
2. Sponsor Mention and Dive into Conversation [00:01:00]: Mention of the episode's sponsor and beginning of the main conversation.
3. Sandy's Angel Investment in Palantir [00:02:00]: Sandy's experience investing in Palantir during the 2009 financial crisis.
4. Discussion on Angel Investing and Financial Risks [00:04:00]: Reflections on angel investing and approach to financial risks.
5. Sandy's Financial Confidence and Investment Strategy [00:05:00]: Sandy's investment rationale and financial confidence.
6. Sandy's Approach to Angel Investing [00:06:00]: Emphasis on having 'skin in the game' and identifying investment opportunities.
7. Journey into Venture Capital and Dual Roles [00:09:00]: Sandy's transition into full-time venture capitalism.
8. Transition to Full-time Venture Capitalist [00:10:00]: Establishment of Horizon VC and full focus on venture capitalism.
9. Decision to Manage Other People's Money [00:11:00]: Shifting from personal investments to managing a fund.
10. Fundraising and Incentive Structures [00:12:00]: Strategy behind fundraising for Horizon VC and alignment with investors.
11. Raising the Fund and Building Relationships [00:14:00]: Process of raising the fund and dynamics of securing commitments.
12. First External Commitment to the Fund [00:15:00]: Sandy's confidence in receiving commitments from his network.
13. Importance of Trust in Fundraising [00:16:00]: The significance of trust in the fundraising process.
14. No Cold Outbounds and Fundraising Dynamics [00:17:00]: Relying on established relationships and trust in fundraising.
15. Fund's Growth and Progress [00:19:00]: Growth of Horizon VC's fund to $44 million by 2022.
16. Investment Thesis and Strategy [00:20:00]: Focus on software startups and the Product-Led-Growth model.
17. Pitching to Investors [00:21:00]: Value proposition offered to potential investors.
18. Focus on Value Creation [00:22:00]: Importance of startups focusing on value creation.
19. Current Market Dynamics for Pre-Seed and Seed Deals [00:24:00]: Current competition in the pre-seed and seed investment landscape.
20. Challenges with Bigger Seed Rounds [00:25:00]: Implications of larger seed rounds at higher valuations.
21. Current Venture Landscape and Future Planning [00:26:00]: The crowded seed investment market and its implications.
22. Planning for Horizon VC's Fund Two [00:28:00]: Potential of launching a second fund.
23. Team Expansion and Firm Building [00:29:00]: Considerations around expanding the Horizon VC team.
24. Considerations for Firm Building [00:30:00]: Potential expansion of Horizon VC.
25. Transition from Angel Investing to Managing LP Money [00:31:00]: The dynamics of managing LP investments.
26. Rapid Fire Questions: Personal Insights [00:32:00]: Getting to know Sandy better.
27. Concluding Remarks and Gratitude [00:34:00]: Sandy's gratitude towards his parents and concluding the episode.

You can find Sandy Kory on Twitter at https://twitter.com/sandykory and learn more about Horizon VC at https://horizon.vc.

Learn more about Flowlie and how the platform can help you screen deals faster and discover the right connections from your network at https://www.flowlie.com.

Stay up-to-date with all our episodes by checking our website at https://www.thevcarchitects.com, following us on Twitter at https://twitter.com/thevcarchitects, and on Instagram at https://www.instagram.com/thevcarchitects.