Kevin Siskar Kevin Siskar

Where Did All the Veterans Go?

With Veterans Day upon us, I’ve had some thoughts. Maybe they provide some insight into the shifting cultural fabric of the United States—or maybe not. Either way, I found the data compelling.

With Veterans Day upon us, I’ve had some thoughts. Maybe they provide some insight into the shifting cultural fabric of the United States—or maybe not. Either way, I found the data compelling.

On Memorial Day earlier this year, I attended a ceremony held by the local legion post in my hometown. It’s a tradition I've participated in since I was a kid, typically involving a small parade with the local volunteer fire company, gun salute, a moment of silence, and veterans from the local legion post paying their respects. But this time, something was different. Fewer than ten veterans were present. The parade, usually a fixture of the event, was canceled because the few veterans who were able to attend either couldn’t—or chose not to—walk the short parade route.

Local Legion Post Memorial Day Service. 

Seeing the dwindling number of attendees led me to wonder, "Where did all the veterans go?" This legion post was mostly veterans from World War II, Vietnam, and the Korean War. And it appeared there was almost no participation from younger veterans of Desert Storm, Afghanistan, or Iraq. So my curiosity got the best of me and I started to google the data to figure out what was going on.

According to PEW Research in November 2023, there are 18 million living veterans in the United States. In 1980, about 18% of U.S. adults were veterans, while today veterans represent about 6% of the country’s adult population.

In 2024, the veteran population has continued to decline. Veterans of the Gulf War era now represent the largest living segment of veterans, while the numbers from earlier conflicts are rapidly decreasing. Only around 100,000 World War II veterans remain, representing less than 1% of the current veteran population. The Department of Veterans Affairs estimates that the number of veterans will drop from today’s 18.3 million to 12.1 million in 2048 – a decrease of about 34%.

Interestingly, the decrease in veterans is also mirrored in our government. The percentage of congressional members who have served in the military is at a historic low, with only 18% of representatives and 17% of senators having military experience. This is a dramatic change from just a few decades ago, when more than three-quarters of Congress had worn the uniform.

I can’t help but feel that the steady decline in the veteran population reflects a larger cultural shift in America. The experiences of older generations—those who lived through the world wars or came of age during the draft—are no longer shared by the majority. Fewer families have a direct connection to military service, which can affect our collective understanding of the sacrifices made and the experiences lived by those who have served.

Supporting Veterans in New Ways:

Despite these shifts, I am encouraged by innovative ways to support and engage with the veteran community, like The Veteran Fund. This venture capital fund invests in military veterans starting companies, creating pathways for veterans to make impactful contributions outside of military service. At Finta, we recently hosted a panel as part of LA Tech Week, where David Kervin‍, a Venture Fund portfolio company joined us. David is the veteran founder of Proteus Space, which is revolutionizing satellite design with AI-driven platforms to reduce the time and cost of deploying satellites through automation and cutting-edge technology. You can take a listen to the event here.

a16z has also raised a fund supporting what a thesis they have coined as “American Dynamism”, which invests in founders and companies that support the national interest. Believing that mission-driven and civic-minded founders often build companies that transcend verticals and business models in their quest to solve important national problems.

Organizations like these help preserve the resilience, ingenuity, and dedication that veterans bring to our society.

I want to be clear: this reflection is not about advocating for war. I’m sensitive to the global conflicts that continue to impact people’s lives, often in devastating ways. Instead, I am simply reflecting on a cultural awareness, noticing that a part of our nation’s past identity might be slowly fading. The decline in the veteran population speaks to a shift away from the collective experience of service that once helped to shape our country. It's a reminder of how fragile and precious the values of service and sacrifice truly are.

This Veterans Day, I want to extend a heartfelt thank you to all veterans. Your service and sacrifice are fundamental parts of our nation’s story. Though the faces of America’s veteran community may be fewer, your contributions endure and continue to shape the lives of many. Thank you for your courage, resilience, and unwavering dedication.

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Fundraising Kevin Siskar Fundraising Kevin Siskar

Fundraising In 2024 - Three Sides Of The Table

During NY Tech Week 2024 Finta 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.

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.

Take A Listen To The Event:

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 startups. Rachel and David emphasize the importance of understanding sector-specific milestones and investor expectations.

The End of Software...?

The panel debates whether the software market has matured. Rachel argues that while the market is evolving, there is still significant upside potential for innovative software solutions, particularly those integrating AI.

Hosting this event was a blast! A massive thank you to everyone who helped make this event happen and a success. We can't wait to see you all at the next one!

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Life Kevin Siskar Life Kevin Siskar

Memento Mori: 117 Billion People

Over 100+ billion humans have existed before us… Everyday we drive on roads, enter buildings, use technology, medicine and science whose existence is the result of contributions by billions of human lives that have come before us.

Over 100+ billion humans have existed before us…

When I first heard this number a few years ago, it was kind of mind blowing. Everyday we drive on roads, enter buildings, use technology, medicine and science whose existence is the result of contributions by billions of human lives that have come before us. We stand on the shoulders of 100+ billion humans who are no longer with us.

117 billion humans to be exact. Recent discoveries suggest that modern Homo sapiens existed much earlier than previously thought, around 200,000 B.C.E. This major shift in our understanding of human existence has led to the estimation that about 117 billion members of our species have ever been born on Earth. When considering this vast number, it's humbling to think about our individual significance and the marks we leave behind. But also, motivational, in some ways as well. In the words of the late Steve Jobs during his famous Stanford Commencement speech,

"Remembering that I'll be dead soon is the most important tool I've ever encountered to help me make the big choices in life. Almost everything—all external expectations, all pride, all fear of embarrassment or failure—these things just fall away in the face of death, leaving only what is truly important."

This perspective, deeply rooted in the Latin phrase Memento Mori, which translates to "remember you must die," serves as a powerful reminder of our mortality and the urgency to focus on what truly matters. Reflecting on how we can truly have a lasting legacy.

So how many humans are there alive today? As of 2024, the world population stands at 8.1 billion, reaching 8 billion in November 2022. It had taken all of human history until around 1800 for world population to reach one billion, the second billion was achieved in only 130 years (1930) thanks to the industrial revolution, the third billion in 30 years (1960), the fourth billion in 15 years (1974), and the fifth billion in only 13 years (1987). Society reached six billion in 11 years (1998), followed by seven billion in 12 years (2010).

During the 20th century alone, the population in the world has grown from 1.65 billion to 6 billion. In 1970, there were roughly half as many people in the world as there are now.

So what does being in the mix with 8 billion other people mean for our ability to leave a mark on the world? Well quite a lot actually, as there is a second historical trend happening at the same time as our explosive world population growth; the rise of the internet.

As of 2024 internet users worldwide reached 5.35 billion, only 66.2% of the global population. This number is expected to rise to 6.54 billion by 2025, thanks to the spread of internet access through affordable mobile phones. From a mere 1.97 billion internet users in June 2010, this growth is nothing short of revolutionary. For context, that means only 1/3 of people now online had internet access when most of us in the tech community had already started tweeting in the late 2000’s…

The finite nature of our time on earth is undeniable. Yet, it's this very limitation that underscores the unprecedented opportunity available to us today. With today's connectivity, individuals have the potential to impact lives on a scale never before imaginable. From sharing knowledge to fostering global movements, the digital age is democratizing influence.

Personally, I'm on a mission to use my time to improve the lives of at least 1 billion people. I’ve shared this goal before in my previous reflections, and it is grounded in the belief that by helping founders and innovators reach their potential, their creations can, in turn, benefit humanity at large, thus improving the lives of 1 billion. It's a mission that I'm deeply passionate about.

In the grand scheme of the universe's timeline, our lives are but brief flickers of existence. Yet, it's within this brevity that we find our most profound opportunity to make an impact. The digital age has gifted us with tools of unprecedented power—the power to connect, to share, and to change the world in ways we're just beginning to understand.

As we navigate this golden age of connectivity, let’s carry the essence of Memento Mori with us—not as a morbid fixation on death, but as a vibrant call to live fully and to leave an indelible positive mark on the tapestry of humanity.

So, what will your impact be? How will you use the precious time you have to create, inspire, and transform the world around you? The clock is ticking, and the digital stage is set. The only question that remains is, what will you do with this unparalleled moment in human history?

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Venture Capital Kevin Siskar Venture Capital Kevin Siskar

Finta is on Product Hunt Today!

Finta is on Product Hunt today! 🥳 We are constantly improving the product with your feedback. So very grateful to the Product Hunt community today and massively appreciate any upvotes! 😻

Finta is on Product Hunt today! 🥳 We are constantly improving the product with your feedback. So very grateful to the Product Hunt community today and massively appreciate any upvotes! 😻

We have been building Finta to be your one fundraising app to replace them all - giving users all the tools they need to streamline the fundraising process end to end so that founders can focus on building real investor relationships. We’ve been working on building and growing Finta over the last year and we’ve had a fantastic response from our users so far. We’re proud to say that we’ve helped founders raise millions of dollars!

In addition to our (actually useful) free-forever plan features, we’re giving a FREE MONTH OF PREMIUM FEATURES for our Product Hunt launch! We now have:

✅ Secure deal rooms that can be shared with a single link.
✅ Deal rooms allow you to attach and include due diligence docs in a single place.
✅ Automated CRM that moves contacts through the funnel automatically as they use your deal room.
✅ Automatic scriptwriting for your email outreach.
✅ Investor database that you can get matched with the best quality investors for your company.
… and a lot more!

Would love to know your thoughts and any feedback, as we are constantly improving Finta and your feedback will have a big impact :) Thank you so much!

Product Hunt is a curation of the best new products, every day. Letting you discover the latest mobile apps, websites, and technology products that everyone's talking about. Thank you again for your constant support!. 

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How Lorenzo Thione Is Scaling Support For Diverse Founders With Gaingels

Lorenzo Thione is 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 Thione, Managing Director of Gaingels

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:


Ambition Today Is Proudly Independent & Supported By:

Finta - Finta’s end to end fundraising management platform enables you to manage your investors throughout their entire lifecycle in a single streamlined flow.

A-List: After every episode of the Ambition Today podcast we record an exclusive bonus clip, where we ask each guest to tell us the best advice they have ever received. Hear first-hand stories from over 30 entrepreneurs and investors in these exclusive bonus clips.


Listen to Ambition Today now: 


Thank you for listening! 

Thank you so much for listening and applying these useful tips and strategies to your life! If you have a chance, please drop by and leave a review for the show on iTunes by clicking here. Also, who should I interview next? Please let me know on Twitter or in the comments. Do you enjoy this podcast? If so, please leave a short review in the comments below. It keeps me going! 🤗

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Millennial Investing Podcast Episode: Venture Capital Investing With Kevin Siskar

Last month I had the opportunity to sit on the opposite sit of the podcaster’s table to be a guest on the Millennial Investing Podcast! Where hosts, Robert Leonard and Clay Finck interview successful entrepreneurs, business leaders, and investors to help educate and inspire the millennial generation.

Kevin Siskar, Millenial Investing Podcast

Recently, I had the opportunity to sit on the opposite sit of the podcaster’s table to be a guest on the Millennial Investing Podcast! Where hosts, Robert Leonard and Clay Finck interview successful entrepreneurs, business leaders, and investors to help educate and inspire the millennial generation.

I hope you enjoy the episode. Listen here!

Host Clay Finck chats with Kevin Siskar about venture capital investing, the types of companies emerging in the venture capital space, how studying human behavior can help you as an investor, the differences between working at a large corporation vs a smaller company, how you can shift yourself to have a growth mindset, how luck has played into the companies Kevin has worked with, and much, much more!

Topics Discussed:

·  What types of companies 43North looks to invest in.

·  Why tech incubators should be everywhere, not just in Silicon Valley.

·  What types of industries are currently most exciting from Kevin’s point of view.

·  How studying human behavior can help you as an investor.

·  What Kevin wishes he could tell his younger self about investing in startups.

·  The differences between working at a large corporation and working at a smaller company.

·  How people can shift from a worker mindset to a growth mindset.

·  How luck has played into the companies that Kevin has worked with.

·  The importance of a strong network and how Kevin maintains such a wide network.

·  And much, much more!

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How Jordan Levy Left His Mark On The Venture Capital Industry

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 Levy | SEed Capital Partners (SBNY)

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:


Ambition Today Is Proudly Independent & Supported By:

Finta - Finta’s end to end fundraising management platform enables you to manage your investors throughout their entire lifecycle in a single streamlined flow.

A-List: After every episode of the Ambition Today podcast we record an exclusive bonus clip, where we ask each guest to tell us the best advice they have ever received. Hear first-hand stories from over 30 entrepreneurs and investors in these exclusive bonus clips.


Listen to Ambition Today now: 


Thank you for listening! 

Thank you so much for listening and applying these useful tips and strategies to your life! If you have a chance, please drop by and leave a review for the show on iTunes by clicking here. Also, who should I interview next? Please let me know on Twitter or in the comments. Do you enjoy this podcast? If so, please leave a short review in the comments below. It keeps me going! 🤗

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Motivation, Productivity, Skillshare, Automation Kevin Siskar Motivation, Productivity, Skillshare, Automation Kevin Siskar

Productivity Today: Finding Your Flow for Maximal Productivity

Flow can transform your experience at work, as well as your productivity, satisfaction, and happiness. While there is no hard and fast rules for inducing flow, there are ways for you to recreate meaningful flow in your life. Join me as I share my methods for unlocking your potential at work and setting yourself up to be more productive with flow.

Surprise! I actually created two new classes with Skillshare this year and this one is all about how to enter the flow state of mind while working!

Flow is the state of being fully in the moment and completely immersed in an activity to the point of effectively disappearing into it. In it, there’s no conscious division between the doer and what’s being done—there’s only the doing.

Flow can transform your experience at work, as well as your productivity, satisfaction, and happiness. While there is no hard and fast rules for inducing flow, there are ways for you to recreate meaningful flow in your life. Join me as I share my methods for unlocking your potential at work and setting yourself up to be more productive with flow. You can take the online class for free here. 

Together, you will:

  • Understand the meaning of flow

  • Find where flow already exists in your life

  • Analyze flow themes and build your personal flow strategy

  • Share these strategies amongst your team and encourage others to reach their full potential

A 10-year McKinsey study on flow and productivity found that top executives are five times more productive during flow. That’s a 500% increase in productivity.

Whether you’d like to increase your productivity at work or simply find joy in what you do, this class will provide you with the tools to harness flow in any scenario. I hope it helps and that you truly enjoy this masterclass in finding focus.

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Motivation, Productivity, Skillshare, Automation Kevin Siskar Motivation, Productivity, Skillshare, Automation Kevin Siskar

Productivity Optimization: Tips and Tools for Automating Your Workflows

Automation softwares are so important for becoming more efficient and creating meaningful output across your team. Join Kevin as he shares top productivity tools for automating your workflows, enabling you to refocus your energy on what you're passionate about and become the best version of yourself.

With over 55,000 students and over 1 million minutes watched on my previous Skillshare classes, I am excited to announce my newest class on how to set up workflow automations!

Automation softwares are so important for becoming more efficient and creating meaningful output across your team. Join me as I share top productivity tools for automating your workflows, enabling you to refocus your energy on what you're passionate about and become the best version of yourself. You can take the class free here. 

Together, you will learn how to:

  • Measure your time in order to maximize your ROI

  • Determine the automation opportunities within your workflows

  • Plan and build your workflow automation, with tools like Zapier.

  • Re-measure your ROI to ensure you are actually saving time and energy

  • Maintain and monitor your automations for long term success

Whether you’re in a leadership position on your team or just starting out, this class will provide you with the tools to focus on what really matters and exercise your creativity in the process. I hope it helps and that you enjoy this automation masterclass.

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Trends Kevin Siskar Trends Kevin Siskar

My 2022 Predictions

Happy New Year to you and your family! In addition to well wishes for 2022, I also wanted to take a minute to kick off 2022 with some predictions for the year! Some of my own, but also let you know what predictions I am following from others.

Happy New Year to you and your family! In addition to well wishes for 2022, I also wanted to take a minute to kick off 2022 with some predictions for the year! Some of my own, but also let you know what predictions I am following from others.

Visited Moraine Lake in Alberta, Canada in 2021.

An investment theme I am closely watching as we head into 2022?

The Artificial Intelligence tools & APIs recently released for software developers enable an entirely new level of automation for software platforms. One example, GPT-3 is a text-based A.I. model from Elon Musk & Sam Altman’s company Open AI that you simply prompt with plain English text, and it will generate an incredibly accurate response. What is fascinating to me is how these AI models continuously improve, to the point that GPT-3 can now even code portions of your app for you, from something as simple as a prompt that says “create a user signup screen.” And within a few seconds, GPT-3 will write all the code, and the browser will render the page with a brand new, fully functioning signup screen. This simplicity and open access will unlock the door for a whole new generation of founders and builders.

What's a trend that is buzzy but will take some time in 2022?

Everyone is talking about the impending third phase of the internet called Web3, which the builders and users decentrally own, orchestrated with tokens. I love the concept of Decentralized Autonomous Organizations or DAOs as I believe they could be the next evolution of what a company is.

I do think the path blockchain technology is on will take the internet closer to this Web3 vision of the future. However, I have spent some time personally building in this space with my company Finta, which provides fundraising software to founders and diligence tools to investors. Finta originally started as a project called Equity Token and through that work, I have seen firsthand how important it is going to be for the SEC to modernize and clarify its securities regulations for a world where tokens can flow freely in a decentralized environment while still representing equity ownership.

Andresson Horowitz recently advocated that the U.S. government create some policy guidance for entrepreneurs to build within. Otherwise, these web3 innovations might happen outside U.S. borders.

What's a development in fundraising founders should know?

Venture Capital is at an all-time high. According to Crunchbase, “prior to 2021, global funding had not reached over $100 billion in a single quarter. Funding in 2021 has far superseded that amount, with the first quarter tracking at $135 billion, the second quarter reaching $159 billion, and the most recent quarter peaking at $160 billion.” 

While access to capital is at an all-time high, and we live in a world where fundraising announcements receive constant glory in the press, the outside appearance to other startup founders can be that fundraising rounds constantly happen with little effort. But the data show’s that most founders log over 100 meetings with different investors to eventually secure the investment they need to safely have 18-24 months of runway in front of the company.

So I want founders to remember that they are not alone and should keep fundraising beyond any initial rejections. Don’t take the rejection personally and use the feedback to improve your pitch for the next investor. I find it has been helpful to get founders into the mindset of thinking about the fundraising process more like a sales process, but this time the product is just different. Instead of a good, you are selling equity in your company. The right investors for your company are out there; you just need to find them so they know you exist. Keep going!

Other 2022 Tech Predictions I Am Following:

  1. Scott Belsky, the founder of Behance and Chief Product Officer at Adobe, put out a great article yesterday on the “10 Forecasts For The Near Future Of Tech”.

  2. Every year Fred Wilson publishes his predictions for the next year and here is Fred’s predictions for 2022. I have to agree that the carbon and climate tech spaces are def heating up, from what I am seeing. What I love about how Fred does this each year is that he also recaps what he got right and wrong the previous year. You can read his 2021 as well.

  3. Finally, The All In Podcast has become one of my favorite listens this past year, and the besties released their tech predictions for 2022 in the latest episode, which you can watch on Youtube or listen to the podcast. The whole episode is good, but a great segment worth listening to on payment rails in fintech, starting at the 27 min mark.

I hope you enjoy the new year and wish you the best of luck in 2022!

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Scott Wayman's Plan for Kangarootime to Support the $648 Billion Care Economy

From a 6 year old calling around on car repairs for his mother, to a thriving CEO of Kangarootime, our next guest Scott Wayman gives us insight on how he got to where he is today. Scott was the oldest son of 24 kids (18 of which were adopted).

Scott Wayman | Kangarootime

Scott Wayman's shares his very 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.

Topics Discussed:

  • A unique upbringing with 18 adopted siblings.

  • Building his sales chops with Enterprise Rental Car.

  • Why you need passion to succeed in your startup’s vision.

  • Kangarootime’s origin story.

  • The role of psychology in startups.

  • How Kangarootime seized a leadership role by helping their daycare centers through COVID19.

  • The future of the $648 Billion Care Economy.

Quote of the Episode:

“Working in a center and living the life of our customers… was crucial to finding product-market fit”

The Greatest Piece of Advice:

Check out the podcast’s backchannel, The A-List , where you can listen to free exclusive audio clips containing the single greatest piece of advice each guest has ever learned!


Links & show notes from this episode:


Ambition Today Is Proudly Independent & Supported By:

Finta - Finta’s end to end fundraising management platform enables you to manage your investors throughout their entire lifecycle in a single streamlined flow.

A-List: After every episode of the Ambition Today podcast we record an exclusive bonus clip, where we ask each guest to tell us the best advice they have ever received. Hear first-hand stories from over 30 entrepreneurs and investors in these exclusive bonus clips.


Listen to Ambition Today now: 


Thank you for listening! 

Thank you so much for listening and applying these useful tips and strategies to your life! If you have a chance, please drop by and leave a review for the show on iTunes by clicking here. Also, who should I interview next? Please let me know on Twitter or in the comments. Do you enjoy this podcast? If so, please leave a short review in the comments below. It keeps me going! 🤗

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Angel Investing, Fundraising Kevin Siskar Angel Investing, Fundraising Kevin Siskar

Introducing Firehouse Ventures 🔥

The past few years I have been quietly building an AngelList Syndicate to share co-investment opportunities for some of my favorite companies. We are calling our syndicate, Firehouse Ventures, a constant reminder to serve the community of founders and never forget that without them (the relentless community of builders), we would be nothing. Here’s to the crazy ones. 🔥

The past few years I have been quietly building an AngelList Syndicate to share co-investment opportunities for some of my favorite companies. When you back a syndicate, you're under no obligation to invest in any deals. You are just committing to keeping any information you receive private and confidential. If you are interested in learning more, just drop your name and email at the button below (and keep reading if you are interested in the back story):


For over 8 years of my pre-New York City life, I was a volunteer fireman with the Swormville Fire Company. I went in burning buildings, ran transports as an EMT, worked up to the rank of Lieutenant, and served the local community 24 hours per day, 7 days per week. My hope was that I was making a meaningful impact on the people of my local community. I wanted to use my time on this planet to make a dent in the world and leave my mark.

One of the reasons I got into startups and venture capital almost a decade ago, was that I saw it as a way to make an even larger impact on the world. Startups were starting to touch the lives of billions of people. I thought, if I could help the founders do that better, then I could (through some magical butterfly effect) help improve the lives of billions of people. I saw venture capital as a way to have my time, serve a larger community and make a larger impact.

The funds & investors that I looked up to most, a decade ago, were predominantly founder and team-focused. Now you would call the stage they played at Pre-Seed and they called themselves “Super Angels” as that term didn’t exist yet.

It’s no secret that in the last decade, the venture capital industry has been the fastest-growing segment of the private capital industry. With lots of new entrants, the industry evolves every few years and we see new styles of investment. For example, Tiger Global is currently re-writing the playbook by playing a different game than how venture capital has been traditionally done. And Covid has also created “An Unpredictable Reopening In Venture Capital”, which Semil Shah of Haystack recently summed up nicely.

But to me, one thing still stays true throughout all of Venture Capital’s evolution. The people are what make the organizations truly excel. And just how the Firemen are there to serve the people of the community, Venture Capitalists are in the business of serving kickass founders. To keep the structures upright when a crisis happens. To reassure, when the unexpected occurs. To offer aid when it’s needed the most. And to help put out fires. There is a human connection that was key to my role as a firefighter, and it is still key today to my role as an investor.

During my time at Founder Institute, I was very fortunate to meet and work with Rachel Sheppard, who was the Director of Global Marketing. She helped scale FI to 180+ cities and 65+ countries. Now Rachel is the Director of Ventures at Mars Petcare as well as the Co-Creator of the Female Founder Initiative, supporting women founders from all over the world. With her on the west coast and me on the east coast, we are working together through our joint network of entrepreneurs, venture capital funds, and accelerators, to when we can syndicate our favorite deals.

We are calling our syndicate, Firehouse Ventures, a constant reminder to serve the community of founders and never forget that without them (the relentless community of builders), we would be nothing. Here’s to the crazy ones. 🔥

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43North's $1 Million Investment Opportunity

Now in its seventh year, the competition offers eight new startups a chance to secure up to $1 million in funding and land a spot in 43North’s next cohort. I have joined the team to help select this year’s companies, and we are currently accepting startup applications for $500k to $1m in investment until July 19th! Investing in founders with deep domain expertise and early traction for their high-growth startup!

43North_FINALS_10.30.19_NancyJParisi_5928.jpg

Being born and raised in Buffalo, NY, I have always loved my hometown city. If you are curious about why, I recommend you check out “The Incredible History of Buffalo, NY In 5 Minutes”, which I shared in the Huffington Post a few years ago.

Scott Wayman of Kangarootime, after winning 43North in 2017

Scott Wayman of Kangarootime, after winning 43North in 2017

In 2014, Buffalo started 43North, investing $5M per year to attract and retain high-growth companies in Buffalo, NY. Fast forward to 2017, and after meeting Scott Wayman, the founder of Kangarootime, at a Founder Institute event in Silicon Valley, I recommended the company to 43North. Kangarootime ran with it and crushed it. First, securing an initial $500k investment from 43North, and then subsequently more follow on funding. They have since grown a significant presence in Western New York and continuing to build a great company! 

Then in 2018, one of my Founder Institute New York portfolio companies, Teddy Mozart, received a large purchase order from QVC. A massive break, but they needed help financing the inventory to fill the QVC order. Carlton, the founder, told me he found Kickfurther, which secures inventory funding via their marketplace of investors. Through Kickfurther, Teddy Mozart managed to get the funds needed to fill the QVC order in less than 72 hours! I told this story while helping to deliberate the final investment decision in 2018, and I like to think it helped play a role in Kickfurther joining the 43N portfolio that year! 

Now in its seventh year, the competition offers eight new startups a chance to secure up to $1 million in funding and land a spot in 43North’s next cohort. I have joined the team to help select this year’s companies, and we are currently accepting startup applications for $500k to $1m in investment until July 19th! Investing in founders with deep domain expertise and early traction for their high-growth startup! 

If you or someone you know might be a good fit, visit 43 North to apply, or feel free to text me at +1 (646) 907-6669 if you would like to connect directly about the opportunity!

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Productivity, Remote Kevin Siskar Productivity, Remote Kevin Siskar

Taking Your Team Remote: People, Process, and Tools

Remote work is quickly becoming normalized and ubiquitous all around the world. Companies are learning that they can now access talent from anywhere globally; while team members are currently building new habits in their day to day workflows. As a leader, it is imperative to make sure your organization is optimized for the next decade of work where results matter much more than a physical location. This course will teach you the foundational steps best to operate any team in a remote work environment. We will be exploring the three main focus areas for building strong remote work environments.

A few years ago I taught a free online class on Skillshare called Productivity Today. Since then over 45,000 people have taken the class and watched over 1 million minutes! So when Skillshare asked me to work together again earlier this year I was excited to partner on a new class.

This past year, like many companies, we transitioned Finta from an office setting in New York’s financial district to a remote organization. It was a transition that was not easy and required meaningful work, but in the long run, we are a better and stronger organization for it. I am excited to share the lessons we have learned as a company in this new class:

Taking Your Team Remote: People, Process, and Tools

Remote work is quickly becoming normalized and ubiquitous all around the world. Companies are learning that they can now access talent from anywhere globally; while team members are currently building new habits in their day to day workflows. As a leader, it is imperative to make sure your organization is optimized for the next decade of work where results matter much more than a physical location. 

This course will teach you the foundational steps best to operate any team in a remote work environment. We will be exploring the three main focus areas for building strong remote work environments:

  • People

  • Process

  • Tools

Across each of these areas, we will be including examples and recommendations you can implement immediately with your own team and business.  So you can start operating a strong remote team today! 

The best part is that any tips and tricks to running a strong remote company are actually complementary to running your company in an office setting. So regardless of if you are running a fully remote, hybrid remote model, or completely in-office work environment, this class will help you be a stronger operator, manager, and leader. Let’s get started!


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Kevin Kevin Siskar Kevin Kevin Siskar

Goodbye 2020, Hello 2021!

Each year, I like to write a short post for the New Year. Turns out my last one was in 2019 and I didn’t write one for 2020. We all know how that went, so I figured it was probably in the world’s collective interest for me to write a post for 2021.

Each year, I like to write a short post for the New Year. Turns out my last one was in 2019 and I didn’t write one for 2020. We all know how that went, so I figured it was probably in the world’s collective interest for me to write a post for 2021. 🥳

Siskar Family

I think we can all safely say that 2020 did not go how any of us planned. When we started my new company Finta, we certainly did not anticipate doing so during a global pandemic. When Colleen went into labor with our first child, I had certainly not expected to be kicked out of the delivery room. It has been a wild year. Even with all the unpredictable events of 2020, when I look back on the year, I think there is still a lot of beauty to be seen.

Siskar Family 2

We welcomed Siena into our lives, and I can honestly say, fatherhood was hands down my favorite part of 2020. Watching her explore and learn about the world around her is fascinating to experience. And the smiles she gives us are pretty epic too!

This year we spent a lot more time with family, immediate and extended. Taking a small step back from the constant grind of work & meetings to find a more stable work-life balance is something I am very grateful for this past year.

Speaking of work, we put our heads down at Finta this year, talked to hundreds of founders, and built, built, built product! I am incredibly excited about where we have arrived with the company (and where we plan to go)!

2020 was a year of change for sure. Change that I feel confident has set a strong foundation for 2021. A year which I am looking forward to quite a bit!

I wish you and your family a happy, healthy, and fortunate new year! Thank you so much for being here, and I look forward to sharing some of the exciting work going on behind the scenes, with you very soon! - Kevin

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Creating Data-Driven Founding Sales Leaders With Peter Kazanjy

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.

Peter Kazanjy | Co-Founder of Atrium

Peter Kazanjy | Co-Founder of Atrium

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. Peter Kazanjy 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. In this episode of the podcast, we go deep into how best to optimize early sales for startups companies.

Topics Discussed:

  • Go-to-Market and Marketing Strategies

  • The difference between founding sales and normal sales.

  • Why sales are so critical to early growth.

  • The best tools for sales, revenue, and accounting

  • Maintaining work-life balance as an entrepreneur

Quote of the Episode:

“Three main rules: focus, focus, focus”.

The Greatest Piece of Advice:

Check out the podcast’s backchannel, The A-List where you can listen to exclusive audio clips containing the single greatest piece of advice each guest has ever learned!


Links & show notes from this episode:


Ambition Today Is Proudly Independent & Supported By:

Finta - A secure, cloud-based, deal room platform. Companies quickly set up a deal room and have a blazing fast tool for raising capital. We make sharing company information with investors secure, simple, and automated.

A-List: After every episode of the Ambition Today podcast we record an exclusive bonus clip, where we ask each guest to tell us the best advice they have ever received. Hear first-hand stories from over 30 entrepreneurs and investors in these exclusive bonus clips.


Listen to Ambition Today now: 


Thank you for listening! 

Thank you so much for listening and applying these useful tips and strategies to your life! If you have a chance, please drop by and leave a review for the show on iTunes by clicking here. Also, who should I interview next? Please let me know on Twitter or in the comments. Do you enjoy this podcast? If so, please leave a short review in the comments below. It keeps me going! 🤗

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Jack Greco Helps Build A Unicorn Company In Buffalo, With ACV Auctions

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.

Jack Greco | ACV Auctions

Jack Greco | ACV Auctions

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:


Ambition Today Is Proudly Independent & Supported By:

Finta - A secure, deal room platform for early-stage companies. Quickly set up your company and you’ve got a blazing fast tool for organizing your fundraise and securing your sensitive company information. House your pitch deck, secure your legal documents, organize your cap table, notify target investors, and close deals faster! Finta allows you to raise more, save time, and increase your efficiency.


Listen to Ambition Today now: 


Thank you for listening! 

Thank you so much for listening and applying these useful tips and strategies to your life! If you have a chance, please drop by and leave a review for the show on iTunes by clicking here. Also, who should I interview next? Please let me know on Twitter or in the comments. Do you enjoy this podcast? If so, please leave a short review in the comments below. It keeps me going! 🤗

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Ambition Today, Entrepreneurship, Podcast, News Kevin Siskar Ambition Today, Entrepreneurship, Podcast, News Kevin Siskar

News Roundtable: Future of American Cities and Working From Home

Kevin Siskar and Tim Shisler are at it again, discussing the current news in our world today.

Ambition Today New Roundtable

Kevin Siskar and Tim Shisler are at it again, discussing the current news in our world today. Each person brings one topic to the table and they talk about them both.

The Future of American Cities:

Kevin starts by discussing how he lived in NYC for almost a decade and how he has seen the cost of living increased significantly during that time. Witnessing how commercial real estate investors have increased their rent so much that small shops are no longer able to handle the cost. 50% of all restaurants in NYC are going to close due to COVID 19, with 12,000 being closed already. So many people think big cities might be dying, but looking at the next few years, Tim and Kevin discuss will the city economies be able to come back?

The Rise of Remote Work:

Tim talks about how it was hard for him to transition to remote work once COVID-19 forced a lot of the world’s workforce to remote. Making it work is a lot about having a plan and being diligent about time and how you carve it out. Routine is key. There is a fine line between work life and home life, the separation needs to be balanced. Should you be working at 8pm when you have a significant other? When working in an office, the commute is there to help you shift out of work mode, what do you no longer have that transition time while working from home. This is also the time where it really shines on the people that really care about their work, vs. the people that were just working to have a job. This is a big topic right now, because working from home is definitely not for everyone.


Ambition Today Is Proudly Independent & Supported By:

Finta - A secure, deal room platform for early stage companies. Quickly set up your company and you’ve got a blazing fast tool for organizing your fundraise and securing your sensitive company information. House your pitch deck, secure your legal documents, organize your cap table, notify target investors, and close deals faster! Finta allows you to raise more, save time, and increase your efficiency.

The A-List - Join the podcast’s backchannel for exclusive access to learn the single greatest piece of advice each guest has ever learned! Plus additional Ambition Today content, deeper guest insights, a community of fellow fans, and much more.


Listen to Ambition Today now: 


Thank you for listening! 

Thank you so much for listening and applying these useful tips and strategies to your life! If you have a chance, please drop by and leave a review for the show on iTunes by clicking here. Also, who should I interview next? Please let me know on Twitter or in the comments. Do you enjoy this podcast? If so, please leave a short review in the comments below. It keeps me going! 🤗

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Bringing Back Jeff Wald To Discuss The End Of Jobs

Our next guest is so amazing, we had to interview him a second time! He was on nearly 5 years ago on Episode 8! Jeff Wald is an entrepreneur who has started three technology companies, with his latest company, WorkMarket, being sold to ADP.

Jeff Wald | Author | The End of Jobs

Jeff Wald | Author | The End of Jobs

Our next guest is so amazing, we had to interview him a second time! Jeff Wald was on Ambition Today nearly 5 years ago on Episode 8 and we are bringing him back for episode 62!

Jeff Wald is an entrepreneur who has started three technology companies, and since we last spoke with Jeff, he sold his latest company, WorkMarket, to ADP. Jeff is also a Board Member on the following boards: Steel Connect, Costar Technologies, TransfrVR, Peerless Systems, and Register.com. During this episode we catch up with Jeff and talk about his new book, “The End of Jobs: The Rise of On-Demand Workers and Agile Corporations”. Tune in to hear all about his book as well as statistics regarding the workforce in 2020:

Topics Discussed:

  • His experience selling the company.

  • The impact of remote working.

  • How to create “social squads” in your company.

  • The importance of defining the goal of any meeting.

  • The steps of technological change, mechanization, electrification, computerization and what comes next with robots and AI.

Quote of the Episode:

“Every time {we revolutionize} we ended up with more jobs, at a higher standard of living, with working fewer hours, that is definitively clear through history.” - Jeff Wald

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:


Ambition Today Is Proudly Independent & Supported By:

Finta - A secure, deal room platform for early-stage companies. Quickly set up your company and you’ve got a blazing fast tool for organizing your fundraise and securing your sensitive company information. House your pitch deck, secure your legal documents, organize your cap table, notify target investors, and close deals faster! Finta allows you to raise more, save time, and increase your efficiency.


Listen to Ambition Today now: 


Thank you for listening! 

Thank you so much for listening and applying these useful tips and strategies to your life! If you have a chance, please drop by and leave a review for the show on iTunes by clicking here. Also, who should I interview next? Please let me know on Twitter or in the comments. Do you enjoy this podcast? If so, please leave a short review in the comments below. It keeps me going! 🤗

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Ambition Today, Entrepreneurship, Podcast, News Kevin Siskar Ambition Today, Entrepreneurship, Podcast, News Kevin Siskar

Ambition Today's News Roundtable: R.I.P. to RBG and Facebook

In this new and exciting podcast, Kevin Siskar and Tim Shisler talk about the current events in our world today.

Ambition Today New Roundtable

In this new episode, Kevin Siskar and Tim Shisler discuss the current news in our world today. Each week, each person brings one topic to the table.

This week Tim chose to talk about the sad passing of former Associate Judge, Ruth Bader Ginsburg on September 18, 2020. She passed away after complications of metastatic pancreatic cancer.

And brought Facebook to the table. There are real issues with Facebook. Everything from the false advertising that Facebook is not taking responsibility for, mental health issues stemming from addiction to Facebook, and now election interference! On September, 3rd Facebook came out with their plan on tackling the Election campaigns on their platform.

Tune in to hear what Tim and Kevin have to say about this week’s topics!


Ambition Today Is Proudly Independent & Supported By:

Finta - A secure, deal room platform for early stage companies. Quickly set up your company and you’ve got a blazing fast tool for organizing your fundraise and securing your sensitive company information. House your pitch deck, secure your legal documents, organize your cap table, notify target investors, and close deals faster! Finta allows you to raise more, save time, and increase your efficiency.

The A-List - Join the podcast’s backchannel for exclusive access to learn the single greatest piece of advice each guest has ever learned! Plus additional Ambition Today content, deeper guest insights, a community of fellow fans, and much more.


Listen to Ambition Today now: 


Thank you for listening! 

Thank you so much for listening and applying these useful tips and strategies to your life! If you have a chance, please drop by and leave a review for the show on iTunes by clicking here. Also, who should I interview next? Please let me know on Twitter or in the comments. Do you enjoy this podcast? If so, please leave a short review in the comments below. It keeps me going! 🤗

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