We're privileged to have Dan Reich join us in this episode - a seasoned entrepreneur and investor with an impressive track record of successful exits. From his humble beginnings selling bouncy balls in high school, he's gone on to found and exit companies in diverse sectors including technology and beauty.

In our conversation, Dan talks about the intricacies of startups, fundraising strategies, and the art of pivoting. He shares candid reflections on his experiences with ventures like Spinback, Tula Skincare, and Troops.ai, each representing different industries and fundraising approaches. Whether you're a first-time founder or a veteran entrepreneur, Dan's story and insights offer valuable lessons for navigating the complex world of startups and venture capital.

Here's what you're in for:

• 00:00 Intro

• 05:19 Choosing the right business partners

• 08:38 The power of the internet and social media

• 12:58 Pivoting from beauty to tech

• 31:17 Building on top of Slack and the acquisition by Salesforce

• 37:07 Post-Acquisition experience and building new ventures

• 43:03 Lessons on fundraising and capital allocation

• 53:40 Angel investing and giving back to the startup ecosystem

• 58:14 Outro

This episode is sponsored by ThunderVC, an investment bank for founders by founders.

Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders

Raising debt? Find the perfect lender in minutes here: https://debt.thunder.vc

Get the latest fundraising insights, news, and tips - https://join.thunder.vc

ABOUT DAN REICH

Dan Reich is a serial entrepreneur and investor with a track record of building and exiting successful companies across tech and beauty industries. His notable ventures include TULA Skincare (acquired by Procter & Gamble), Troops.ai (acquired by Salesforce), and Spinback (acquired by Buddy Media, later Salesforce). Dan's entrepreneurial journey, which began in his teens, has earned him recognition as one of the "coolest people in New York tech" by Business Insider.

Beyond his business acumen, Dan is an active angel investor, advisor, and philanthropist. He holds a degree in Electrical Engineering from the University of Wisconsin-Madison and has contributed to publications like Forbes and Harvard Business Review. When not building companies, Dan can be found at New York Giants games, on the golf course, or volunteering for rescue operations at Mount Snow, Vermont. His life philosophy is simple: "I am, and will forever be, a student."

Connect with Dan Reich on:

• Linkedin: https://www.linkedin.com/in/danreich/

• X : https://x.com/DanReich

• Website: https://danreich.com/

  
  

ABOUT FUNDRAISING DEMYSTIFIED

Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.

Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.

ABOUT JASON

Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.

You can reach out to Jason through:

Email: jason@thunder.vc

LinkedIn: https://www.linkedin.com/in/jasonrkirby/

In this episode, we're thrilled to talk with a true tech veteran, Chris Gladwin, a serial entrepreneur and currently the CEO and co-founder of Ocient. Chris shares his journey through multiple successful ventures, including Cleversafe (acquired by IBM for over $1.4 billion) and MusicNow. He provides valuable insights into raising capital, navigating market cycles, and building resilient tech companies.

Chris offers a unique perspective on entrepreneurship, having raised hundreds of millions of dollars across various market conditions. He discusses the challenges of fundraising during different economic climates and shares strategies for success. Whether you're a first-time founder or a seasoned entrepreneur, Chris's practical advice and real-world stories will surely resonate.

Here's what you're in for:

• 00:00 - Intro

• 07:54 - Strategies for raising capital vs. selling companies

• 11:03 - Navigating fundraising in different market cycles

• 23:43 - Understanding valuation models and market trends

• 30:17 - Avoiding overvaluation and excessive burn rates

• 37:38 - The benefits of being bought rather than selling

• 39:35 - How Circuit City acquired Music Now

• 48:35 - Outro

  
  

This episode is sponsored by ThunderVC, an investment bank for founders by founders.

Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders

Raising debt? Find the perfect lender in minutes here: https://debt.thunder.vc

Get the latest fundraising insights, news, and tips - https://join.thunder.vc

ABOUT CHRIS GLADWIN

Chris Gladwin is a seasoned entrepreneur with multiple successful exits under his belt. He is currently the CEO and co-founder of OCIENT, a software company providing solutions for the world's largest data analyzing systems.

In 2004, Chris founded Cleversafe, which became the largest and most strategic object storage vendor in the world. Under his leadership, Cleversafe had over 1,000 patents granted or filed. After raising over $100M, Chris led the company to a $1.4B exit in 2015 when IBM acquired the company.

Before Cleversafe, Chris founded MusicNow and Cruise Technologies startups and led Zenith Data Systems' product strategy. He started his career at Martin Marietta as a database developer and holds an engineering degree from MIT. Chris's experience spans various sectors, including data storage, digital music, and enterprise software, making him a valuable voice in the tech startup ecosystem.

Connect with Chris Gladwin on:

• Linkedin: https://www.linkedin.com/in/chris-gladwin-7ba42b/

• Website: https://ocient.com/

  
  

ABOUT FUNDRAISING DEMYSTIFIED

Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.

Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.

ABOUT JASON

Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.

You can reach out to Jason through:

Email: jason@thunder.vc
LinkedIn: https://www.linkedin.com/in/jasonrkirby/

In this episode, we're sitting down with Alex Pattis, general partner at Riverside Ventures and author of the newsletter "Last Money In". Alex shares his journey from sales director to launching a syndicate that has completed over 300 deals and deployed $75 million in capital.

Alex provides valuable insights into how syndicates operate, their advantages for both founders and investors, and the common pitfalls to avoid. He also discusses the current trends in the syndicate market and offers advice for founders considering working with syndicates.

Here's what you're in for:

• 00: 00 - Intro

• 04:53 - Demystifying syndicates: Understanding LPs and SPVs

• 07:54 - The value of syndicates for founders

• 14:11 - The importance of transparency in the syndicate process

• 18:37 - Current trends in the syndicate market

• 32:36 - Common mistakes in the syndicate market

• 38:01 - Strategic fundraising with Special Purpose Vehicles (SPVs)

• 47:19 - Outro

  
  

This episode is sponsored by ThunderVC, an investment bank for founders by founders.

Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders

Raising debt? Find the perfect lender in minutes here: https://debt.thunder.vc

Get the latest fundraising insights, news, and tips - https://join.thunder.vc

ABOUT ALEX PATTIS

Alex Pattis is a seasoned entrepreneur and investor with a diverse background in both operations and venture capital. He is currently a co-founder of Last Money In Media, producing the most actionable VC newsletter focused on explaining Special Purpose Vehicles within the

Venture Capital ecosystem. He is also a General Partner at Riverside Ventures, an early-stage venture capital firm investing in high-growth technology companies. To date, they have deployed over $70 million.

Alex's operating background includes nearly a decade of scaling early-stage startups, focusing on growth and commercial strategy. In venture capital, Alex has invested in over 250 companies as a General Partner at Riverside Ventures. He is passionate about supporting entrepreneurs in the early stages of their businesses. His experience spans both operational and investment roles, giving him a unique perspective on the startup ecosystem.

Connect with Alex Pattis on:

• Linkedin: https://www.linkedin.com/in/alex-pattis-1709011a/

• Newsletter: https://lastmoneyin.co/

  
  

ABOUT FUNDRAISING DEMYSTIFIED

Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.

Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.

ABOUT JASON

Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.

You can reach out to Jason through:

Email: jason@thunder.vc

LinkedIn: https://www.linkedin.com/in/jasonrkirby/

We're excited to have Wen-Wen Lam, former founder of NexTravel and formerly a partner at Gradient Ventures, join us in this episode. Wen-Wen shares her entrepreneurial journey, from her early days at LinkedIn to founding and scaling NexTravel to $100 million in bookings before the COVID-19 pandemic disrupted the travel industry.

Wen-Wen provides invaluable insights into the challenging process of acquiring and selling a company during a crisis. She walks us through her strategic approach, including compiling a list of potential buyers, pitching the acquisition, and navigating the intense psychological pressures involved which led to the acquisition by Travelperk in 2020. She also talks about the transition into venture capital where she focused on consumer applications of AI in areas like chatbots, the creator economy, and social platforms. Wen-Wen shares her unique perspective on identifying promising startups in these spaces.

Here's what you're in for:

• 00:00 - Intro

• 00:34 - Background and path to founding NexTravel

• 06:59 - Scaling NexTravel to $100 million in bookings

• 10:45 - Impact of COVID-19 and the decision to sell the company

• 16:02 - Strategic approach to running an acquisition process

• 24:44 - Joining Gradient Ventures and her transition into VC

• 32:00 - The rise of chatbots and their appeal to younger generations

• 37:02 - The power of unique and funny content

• 42:00 - Outro

  
  

This episode is sponsored by ThunderVC, an investment bank for founders by founders.

Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders

Raising debt? Find the perfect lender in minutes here: https://debt.thunder.vc

Get the latest fundraising insights, news, and tips - https://join.thunder.vc

ABOUT WEN-WEN LAM

Wen-Wen Lam, a seasoned entrepreneur and investor, was formerly a partner at Gradient Ventures, an AI fund. Prior to joining Gradient, she founded NexTravel, a corporate travel booking platform that scaled to over $100 million in bookings before being acquired by Travelperk during the COVID-19 pandemic. Her resilience and strategic approach allowed her to navigate the challenges of acquiring and selling a company amid a crisis. Wen-Wen's entrepreneurial journey began at LinkedIn and she has also worked with the founders of MySpace at Slingshot Labs, providing her with unique insights into building successful startups, fundraising, and operating in rapidly evolving industries.

With her multifaceted career, Wen-Wen brings a valuable combination of operating experience and investment acumen to Gradient Ventures, focusing on areas like chatbots, the creator economy, and social AI applications.

Connect with Wen-Wen on:

• Linkedin: https://www.linkedin.com/in/wenwen/

• X: https://x.com/wenwen?lang=en

  
  

ABOUT FUNDRAISING DEMYSTIFIED

Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.

Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.

ABOUT JASON

Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.

You can reach out to Jason through:

Email: jason@thunder.vc
LinkedIn: https://www.linkedin.com/in/jasonrkirby/

In this episode, Winter Mead, CEO and founder of Coolwater Capital shares his take on what it takes to support emerging fund managers. Coolwater Capital serves as an accelerator for emerging venture fund managers, offering training, resources, and a supportive cohort model to help them successfully build and scale their firms. He has influenced over 200 fund launches and continually adapting to the dynamic needs of the venture capital market.

We discuss the latest trends in VC funding and the types of fund managers that are currently securing funding. He points out common pitfalls that new fund managers should avoid. Winter also explains the cohort model used by Coolwater to support fund managers, emphasizing the importance of information sharing and strong networks.

Here's what you're in for:

• (00:00) - Intro

• (00:40) - Transition from working as a limited partner to founding Coolwater

• (03:03) - The challenges of starting Coolwater

• (09:06) - How Coolwater evaluates and supports fund managers

• (15:05) - Differences in fundraising for startups vs funds

• (23:22) - Trends in VC funding

• (31:51) - Common mistakes emerging fund managers make

• (47:05) - Profiles of fund managers in Coolwater

• (52:23) - Outro

This episode is sponsored by ThunderVC, an investment bank for founders by founders.

Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders

Raising debt? Find the perfect lender in minutes here: https://debt.thunder.vc

Get the latest fundraising insights, news, and tips - https://join.thunder.vc

ABOUT WINTER MEAD

Winter Mead is the founder and managing member of Coolwater Capital, specializing in emerging managers and technology investments. He authored "How To Raise A Venture Capital Fund" and operates Coolwater, an academy dedicated to training and scaling emerging fund managers. With a history of building an evergreen fund at SAP and working in private equity and venture capital in San Francisco, Winter has made significant contributions to the venture capital community, including founding the LP transparency movement, #OpenLP. He also served as junior faculty at Stanford's Graduate School of Business and holds advanced degrees from the University of Oxford and Harvard University. Winter lives in Utah with his family and is deeply committed to enhancing the capabilities of new managers in the venture capital industry through his work at Coolwater.

Connect with Winter on:

• Linkedin: https://www.linkedin.com/in/wintermead/

• X: https://x.com/wintmead?lang=en

  
  

ABOUT FUNDRAISING DEMYSTIFIED

Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.

Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.

ABOUT JASON

Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 exits and 15 years of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.

You can reach out to Jason through:

Email: jason@thunder.vc

LinkedIn: https://www.linkedin.com/in/jasonrkirby/

We're thrilled to have Diana Heldfond, the solo founder and CEO of Parallel, join us in this episode. Parallel is a cutting-edge virtual care platform focused on aiding children with learning and thinking challenges such as dyslexia and ADHD. Under Diana’s leadership, Parallel has raised over $29 million and now works with numerous school districts across the US, integrating healthcare and education through innovative technology to provide tailored and effective support.

Diana discusses the unique challenges and strategies of fundraising as a solo founder. She talks about how she cultivated early relationships with investors, crafted compelling narratives to manage fundraising timelines effectively, and faced investor rejections head-on. Her strategy shows how crucial it is to be resilient and plan ahead when getting funding alone, without a co-founder.

Here's what you're in for:

00:00 - Intro

00:29 - The mission and vision behind Parallel

02:06 - Diana’s personal motivation for founding Parallel

06:10 - Challenges and triumphs of being a solo founder

09:03 - The strategic decision not to wait for a co-founder

16:03 - Managing both fundraising and company leadership

24:35 - Key performance indicators that attract investors

40:47 - Understanding the process of fundraising and handling rejection

47:59 - Outro

This episode is sponsored by ThunderVC, an investment bank for founders by founders.

Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders

Raising debt? Find the perfect lender in minutes here: https://debt.thunder.vc

Get the latest fundraising insights, news, and tips - https://join.thunder.vc

ABOUT DIANA HELDFOND

Diana Heldfond is the visionary founder and CEO of Parallel, an innovative virtual care platform transforming the delivery of educational and healthcare services. With a background in business and finance, Diana combines her personal experiences and professional expertise to lead Parallel in enhancing educational outcomes for children across America. Her leadership and persistence have not only propelled the company through significant growth phases but also positioned it as a leader in the intersection of tech, education, and healthcare.

Connect with Diana on:

• Linkedin: https://www.linkedin.com/in/diana-heldfond/

• Instagram: https://www.instagram.com/dheldfond/?hl=en

• X: https://twitter.com/dheldfond?lang=en

  
  

ABOUT FUNDRAISING DEMYSTIFIED

Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.

Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.

ABOUT JASON

Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.

You can reach out to Jason through:

Email: jason@thunder.vc

LinkedIn: https://www.linkedin.com/in/jasonrkirby/