Ep. 138 - How To Raise Money and Work with Venture Capitalists

The Conference Room with Simon Lader

In this week's episode of The Conference Room, host Simon Lader sits down with Rick Olesek, A cybersecurity expert and current head of portfolio go-to-market at Gula Tech Adventures. Rick shares his journey from a network security analyst at the NSA to his current role, offering listeners a deep dive into his strategies for building successful go-to-market strategies for early-stage cyber vendors. This episode is packed with practical advice for entrepreneurs looking to scale their businesses and secure venture capital. 01:07 - Rick’s career overview and current role. 03:31 - Transition to Tenable and key contributions. 06:27 - Moving from Tenable to other ventures 08:04 - Rick’s role at Gula Tech Adventures 09:28 - Initial deal flow and evaluation process. 11:51 - Importance of Having a clear go-to-market strategy. 14:13 - Red flags in assessing a company’s investment readiness. 16:37 - The realistic portrayal of VC engagement on shows like Shark Tank. 18:27 - Importance of targeted value propositions in fundraising. 20:22 - Knowing your audience and the importance of tailored pitches. 23:02 - Determining the level of engagement with portfolio companies. 25:13 - The necessity of company evolution and strategic pivots. 26:38 - Importance of Simplifying Messaging. 28:04 - Challenges and Reassessments 29:30 - Importance of Under-promising and Over-delivering 31:30 - Learning from Investment Outcomes 34:03 - Essential Tips for Entrepreneurs 36:15 - Handling NDAs with VCs 38:20 - Transparency and Feedback from VCs 40:00 - Matching VCs to Business Needs 41:22 - Advantages of Complementary Portfolios To learn more about Rick Olesek please visit his Linkedin Profile To learn more about Gula Tech, please visit their website You can also access amazing startup content on the Gulatech Adventures YouTube channel: https://www.youtube.com/@GulaTechAdventures YOUR HOST - SIMON LADER Simon Lader is the host of The Conference Room, Co-Founder of global executive search firm Salisi Human Capital, and lead generation consultancy Flow and Scale. Since 1997, Simon has helped cybersecurity vendors to build highly effective teams, and since 2022 he has helped people create consistent revenue through consistent lead generation. Get to know more about Simon at: Website: https://simonlader.com/ Twitter: https://twitter.com/simonlader LinkedIn: https://www.linkedin.com/in/headhuntersimonlader/ The Conference Room is available on Spotify Apple podcasts Amazon Music IHeartRadio