Ambition Today, Startup Stories with Kevin Siskar Kevin Siskar

During NY Tech Week 2024 we hosted a live panel discussion in midtown Manhattan on the state of fundraising in 2024. Delving deep into the nuances of fundraising from three different perspectives: an investor, a founder, and a lawyer.
Hear from 3 different sides of the table when we gather an investor, founder, and a lawyer to discuss what fundraising venture capital in 2024. Our incredible panel for this event consists of:
​The Founder ‍David Silverstein, is the CEO of Ned, a white label lending platform that makes it easy for lenders to effortlessly deploy capital.
The Investor Rachel ten Brink, General Partner at Red Bike Capital, an early-stage VC fund based in New York, specializing in SaaS, Health & Wellness, and Fintech sectors in the U.S. With over 30 years of experience, including founding a Y Combinator-backed startup that reached $100M in revenue and managing $2B in assets.
The Lawyer ​Jack Sousa, is the Partner & Co-Chair of the Emerging Companies and Venture Capital Practice Group at Wiggin. He is also a wiggin(x) Co-Founder and Partner. Jack focuses his practice on venture capital, startup and early-stage companies and their financing needs.
 
Key Fundraising Insights From This Episode: How Should Founders Think About Fundraising David Silverstein kicked off the event emphasizes the importance of focus during a raise. Trying to shrink the amount of time you spend fundraising so you can get back to building the business. Highlighting the importance of relationship building in fundraising, while de-risking and hitting the right milestones to build trust with investors.
Rachel ten Brink advises founders to start planning their next round of funding as soon as they close their current round. She emphasizes the need to reverse-engineer the process, understanding how far the current funds will take the company and what metrics need to be hit for the next raise.
AI's Influence On Startups AI will fundamentally transform the venture capital landscape. Rachel notes that AI is not just a sector but a foundational technology that will touch every industry. David adds that while AI is important, it is crucial to solve fundamental business problems first.
VC Investor Relations with LP's Rachel discusses the current trends in VC strategies and the importance of understanding the dynamics between VC funds and their LPs. She highlights the necessity for founders to be aware of the financial health and commitments of the VCs they are pitching to.
Current Market Trends and Company Valuations The discussion centers around the importance of always being prepared to fundraise and understanding market dynamics. David stresses the situational nature of fundraising, advising founders to be ready to adapt to market conditions.
Important Fundraising Legal Considerations Jack Sousa recommends involving a lawyer early in the fundraising process to navigate complex legal terms and agreements. He mentions the return of redemption provisions and full ratchet anti-dilution clauses as trends to watch.
How Can Founder's Stand Out To Investors To stand out, David suggests focusing on demonstrating real customer traction and needs. Rachel emphasizes the importance of clear, concise pitch decks and consistent communication with investors.
Strong Investor Communication Balancing warm introductions and cold outreach is crucial. David recommends building relationships with investors before needing to raise funds, while Rachel highlights the importance of thoughtful signaling and avoiding desperate outreach.
Practical Tips for Founders Jack Sousa and Rachel discuss essential legal terms, noting the increasing prevalence of liquidation preferences and full ratchet anti-dilution clauses. They advise founders to keep their cap tables clean and to be aware of the long-term implications of their fundraising choices.
Industry-Specific Insights Raising funds for deep tech ventures involves unique challenges compared to traditional SaaS

We sat down with one of the most influential people in tech, Lorenzo Thione, who shares his very inspiring journey and how that led him to be where he is today.
Lorenzo grew up in Milan, Italy and had a technical background at an early age. He completed his studies at the University of Texas at Austin, from which he holds a M.S. in Computer Engineering.
He is now the Managing Director of Gaingels, a leading LGBTQIA+/Allies investment syndicate and one of the largest and most active private investors in North America. He is also the co-founding Chairman of StartOut, Chairman of the Board at Social Edge, and previously co-founded Powerset, a natural-language search engine startup sold to Microsoft for $100 million in 2008.
Lorenzo is named one of the most influential LGBT people in tech in 2014 and 2018 and his dedication in supporting and elevating leaders of the LGBTQ+ in the venture startup is amazing.
As the Managing Producer at Sing Out, Louis! Productions, he is also a Tony-Award winner (Hadestown, The Inheritance). He produced and co-created the Broadway musical, Allegiance starring George Takei and Lea Salonga. He is currently working in a new original musical, Indigo, as well as The Elephant Whisperer.
We covered a lot of ground in this episode, including:
Topics Discussed:
Where his passion comes from and how Lorenzo found entrepreneurship.
Helping others to build a diverse company by providing more than just funding.
The different companies that he had a part in building.
His mark on Broadway.
How your descent can make a difference in your future and your thinking.
How the model of angel groups is evolving to syndicates and SPV’s.
The role of a “Platform” strategy to help Gaingels portfolio companies.
What does Lorenzo think about the future of Venture Capital.
 
Quote of the Episode:
“Strategic Value, what is all being brought to the table”
 
The Greatest Piece of Advice:
His mentor told him to, “ be obsessive, about how you can add value, to your own network and relationships”

Links & show notes from this episode:
Lorenzo Thione on Bio
Lorenzo Thione on LinkedIn
Lorenzo Thione on Twitter
Gaingels
StartOut
Shearshare
Bryan Janeczko episode
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Visit Ambition Today on the Web: ​www.siskar.co/ambitiontoday Follow Kevin Siskar on Twitter: ​twitter.com/TheSiskar
Follow Kevin Siskar on Instagram: instagram.com/thesiskar
Follow Kevin Siskar on Facebook: facebook.com/kevin.siskar
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Kevin Siskar brings you ambitious entrepreneurs inspired by Tim Ferriss Show, How I Built This with Guy Raz, Residual Income, Entrepreneur on Fire, NPR, HBR, TED Radio Hour, the StartUp podcast with Alex Blumberg by Gimlet Media, Pat Flynn, Tony Robbins, The Uncertain Hour, Bigger Pockets, Art of Charm, Dave Ramsey, Planet Money, Jocko Podcast, EntreLeadership, Zigler, APM Marketplace, This Week In Startups with Jason Calacanis, Mixergy, Seth Godin, Joe Rogan Experience, GaryVee, James Altucher, Monocle 24, How to Start a Startup, Crooked Media, and The $100 MBA Show with Omar Zenhom, and Casey Neistat.
Be sure to listen and subscribe to Ambition Today in the iTunes Store for iOS (apple.co/1NRRPzL), on Google Play Music (goo.gl/LmmciJ), or on Stitcher for Android (bit.ly/1Rn01dy).

In the fall we sat down with one of the godfathers of Venture Capital, Jordan Levy, who shares his very inspiring founder story and how that led to his career as an investor.
Jordan co-founded Software Distribution Services which was acquired by Ingram Micro, before going on to be a Partner on the early-stage investing team at SoftBank Capital (SBNY) for 16 years.
Jordan has served on the boards of BuzzFeed, TalkSpace, Work Market, ACV Auctions, and many others. Using his upbringing and religion to pay it forward (Tzedakah) to the community that he grew up in, in Buffalo, New York. Jordy also co-founded Z80 Labs, a startup incubator in Buffalo, and 43North, an accelerator that hosts an annual startup competition, investing $5M per year in Buffalo, NY. We cover a lot of ground in this episode, including:
 
Topics Discussed:
Building Software Distribution Services in the early days of venture capital.
How to think about the private vs public markets.
The intricacies of SPACs vs the IPO.
Lessons learned from decades of investments.
Betting on the first days of the internet and what has changed since.
Investing through the dot com boom and bust.
How ACV Auctions re-defined the auto market.
The importance of investing in people over markets, trends, and other aspects of the business.
 
Quote of the Episode:
“You invest in the people and I will always believe that” and “if you don’t think someone can take this company to the promised land, then don’t invest in them.”
 
The Greatest Piece of Advice:
As his grandmother passed down to him, “never go to bed angry with your wife.”

Links & show notes from this episode:
Jordan Levy’s Bio
Jordan Levy on LinkedIn
Jordan Levy on Twitter
Finta
43North




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Visit Ambition Today on the Web: ​www.siskar.co/ambitiontoday Follow Kevin Siskar on Twitter: ​twitter.com/TheSiskar
Follow Kevin Siskar on Instagram: instagram.com/thesiskar
Follow Kevin Siskar on Facebook: facebook.com/kevin.siskar
Add Kevin Siskar on Snapchat: snapchat.com/add/krsiskar
Kevin Siskar brings you ambitious entrepreneurs inspired by Tim Ferriss Show, How I Built This with Guy Raz, Residual Income, Entrepreneur on Fire, NPR, HBR, TED Radio Hour, the StartUp podcast with Alex Blumberg by Gimlet Media, Pat Flynn, Tony Robbins, The Uncertain Hour, Bigger Pockets, Art of Charm, Dave Ramsey, Planet Money, Jocko Podcast, EntreLeadership, Zigler, APM Marketplace, This Week In Startups with Jason Calacanis, Mixergy, Seth Godin, Joe Rogan Experience, GaryVee, James Altucher, Monocle 24, How to Start a Startup, Crooked Media, and The $100 MBA Show with Omar Zenhom, and Casey Neistat.
Be sure to listen and subscribe to Ambition Today in the iTunes Store for iOS (apple.co/1NRRPzL), on Google Play Music (goo.gl/LmmciJ), or on Stitcher for Android (bit.ly/1Rn01dy).

Scott Wayman's shares his epically inspiring founder story. His passion for Kangarootime is next level and the company is currently focused on winning the childcare management software space for daycares and preschools. With plans to expand to the larger “care economy” which includes not only early education & childcare but also elder & senior care. A $648B TAM in the U.S. Alone according to Melinda Gate's Pivotal Ventures.
The Kangarootime team brilliantly positioned themselves throughout COVID19 as leaders in the space, by taking time to host educational sessions about how their customers can best adapt their centers, as well as quickly shipping new features such as contactless check-in/out, health checks, and more. I have personally watched Scott relentlessly grow this company from their early days at Founder Institute, through several investments from 43North, and was very excited to sit down with him for this episode.
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Visit Ambition Today on the Web: ​www.siskar.co/ambitiontoday Follow Kevin Siskar on Twitter: ​twitter.com/TheSiskar
Follow Kevin Siskar on Instagram: instagram.com/thesiskar Follow Kevin Siskar on Facebook: facebook.com/kevin.siskar Add Kevin Siskar on Snapchat: snapchat.com/add/krsiskar
Kevin Siskar brings you ambitious entrepreneurs inspired by Tim Ferriss Show, How I Built This with Guy Raz, Residual Income, Entrepreneur on Fire, NPR, HBR, TED Radio Hour, the StartUp podcast with Alex Blumberg by Gimlet Media, Pat Flynn, Tony Robbins, The Uncertain Hour, Bigger Pockets, Art of Charm, Dave Ramsey, Planet Money, Jocko Podcast, EntreLeadership, Zigler, APM Marketplace, This Week In Startups with Jason Calacanis, Mixergy, Seth Godin, Joe Rogan Experience, GaryVee, James Altucher, Monocle 24, How to Start a Startup, Crooked Media, and The $100 MBA Show with Omar Zenhom, and Casey Neistat.
Be sure to listen and subscribe to Ambition Today in the iTunes Store for iOS (apple.co/1NRRPzL), on Google Play Music (goo.gl/LmmciJ), or on Stitcher for Android (bit.ly/1Rn01dy).

Pete Kazanjy is Ambition Today’s new guest from Southern California. He is sitting in San Francisco, CA right now as we speak, enjoying Alamo Square.
He is a serial founder and seasoned early stage Saas executive, advisor, and investor. Pete has cofounded many companies including TalentBin, Modern Sales, and Atrium. He is also an author of “Founding Sales”.
He went to Stanford where he learned English and Philosophy.
Pete is still going strong and has a lot to offer his clients, be sure to read his book “Founding Sales”, a Startup Sales Handbook.
Topics Discussed:
Branding and Design
Go-to-Market and Marketing Strategies
Product Development
Hiring and On-Boarding
Sales, Revenue, and Accounting
Work-life balance
End Game
Quote of the Episode:
“Three main rules: focus, focus, focus”.
The Greatest Piece of Advice:
Checkout the podcast’s back channel, The A-List where you can listen to exclusive audio clips containing the single greatest piece of advice our guests have ever learned!

Links & show notes from this episode:
Atrium
Peter’s Bio
Founding Sales
Connect with Peter on LinkedIn
Connect with Peter on Twitter
Finta




==========
Visit Ambition Today on the Web: ​www.siskar.co/ambitiontoday
Follow Kevin Siskar on Twitter: ​twitter.com/TheSiskar
Follow Kevin Siskar on Instagram: instagram.com/thesiskar
Follow Kevin Siskar on Facebook: facebook.com/kevin.siskar
Add Kevin Siskar on Snapchat: snapchat.com/add/krsiskar
Kevin Siskar brings you ambitious entrepreneurs inspired by Tim Ferriss Show, How I Built This with Guy Raz, Residual Income, Entrepreneur on Fire, NPR, HBR, TED Radio Hour, the StartUp podcast with Alex Blumberg by Gimlet Media, Pat Flynn, Tony Robbins, The Uncertain Hour, Bigger Pockets, Art of Charm, Dave Ramsey, Planet Money, Jocko Podcast, EntreLeadership, Zigler, APM Marketplace, This Week In Startups with Jason Calacanis, Mixergy, Seth Godin, Joe Rogan Experience, GaryVee, James Altucher, Monocle 24, How to Start a Startup, Crooked Media, and The $100 MBA Show with Omar Zenhom, and Casey Neistat.
Be sure to listen and subscribe to Ambition Today in the iTunes Store for iOS (apple.co/1NRRPzL), on Google Play Music (goo.gl/LmmciJ), or on Stitcher for Android (bit.ly/1Rn01dy).

 



From growing up on a dairy farm, to a successful entrepreneur with hundreds of employees, meet our next guest, Jack Greco. Greco co-founded ACV Auctions, an online auction dealer platform, which was last valued at $1.5B. He never thought that he would be the person to co-found Buffalo’s first unicorn startup in 2014. The great part is the story behind his success. He later reveals to Kevin that he has been fired from every job before he became a founder, and what kicked him in gear, was learning that he had a baby on the way. Every success story is different, and I think this is great for our audience to hear, and prove to you, never give up, or think that you are not worth something because you got fired! Pick your feet up and move on!
As of 2018, Greco left ACV Auctions and is now an angel investor. To date, he has invested in over 50 companies and is trying his hardest to maintain a quality work-life balance for his son.
Topics Discussed:
A little background on Jack Greco
Unicorn Start-Up
Angel investing in 50 companies
Working with others
Covid effects on the world
Work-life balance
Mental Health
Having a coach is so important
Buffalo Bridge
Quote of the Episode:
“This [ACV Auctions] is a great learning experience, and it will shape who I am going to be as an investor, a mentor, executive, father, for the rest of my life.” - Jack Greco
The Greatest Piece of Advice:
Checkout the podcast’s back channel, The A-List where you can listen to exclusive audio clips containing the single greatest piece of advice our guests have ever learned!

Links & show notes from this episode:
ACV Auctions
Connect with Jack on LinkedIn
Connect with Jack on Twitter
Buffalo Bridge
Finta
==========
Visit Ambition Today on the Web: ​www.siskar.co/ambitiontoday
Follow Kevin Siskar on Twitter: ​twitter.com/TheSiskar
Follow Kevin Siskar on Instagram: instagram.com/thesiskar
Follow Kevin Siskar on Facebook: facebook.com/kevin.siskar
Add Kevin Siskar on Snapchat: snapchat.com/add/krsiskar
Kevin Siskar brings you ambitious entrepreneurs inspired by Tim Ferriss Show, How I Built This with Guy Raz, Residual Income, Entrepreneur on Fire, NPR, HBR, TED Radio Hour, the StartUp podcast with Alex Blumberg by Gimlet Media, Pat Flynn, Tony Robbins, The Uncertain Hour, Bigger Pockets, Art of Charm, Dave Ramsey, Planet Money, Jocko Podcast, EntreLeadership, Zigler, APM Marketplace, This Week In Startups with Jason Calacanis, Mixergy, Seth Godin, Joe Rogan Experience, GaryVee, James Altucher, Monocle 24, How to Start a Startup, Crooked Media, and The $100 MBA Show with Omar Zenhom, and Casey Neistat.
Be sure to listen and subscribe to Ambition Today in the iTunes Store for iOS (apple.co/1NRRPzL), on Google Play Music (goo.gl/LmmciJ), or on Stitcher for Android (bit.ly/1Rn01dy).