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The Capital Stack

Latest episodes

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Apr 11, 2023 • 32min

Roberto Guerrieri and Stuart Illian of BlueTail on Digital Transformation in Vertical SaaS and Working with Unstructured Data

What does it take to build and scale a vertical SaaS company? The process of building and scaling a vertical SaaS company requires customer research, continuous tech development, and being flexible to potential changes along the way.In this episode of The Capital Stack, we have Roberto Guerrieri and Stuart Illian, the co-founders of Bluetail, a vertical SaaS company for aircraft owners that digitizes back-to-birth paper records and turns them into protected, searchable, and shareable assets.Listen in to learn about the journey of a startup and how you can end up in a different place from where you initially thought. You will also learn about the evangelizing and outreach that goes into selling a vertical SaaS product geared toward digital transformation.What You Will Discover:·       [00:00] Intro·       [01:50] Stuart on how they came up with the idea of digitizing flight records from static to structured information.·       [06:53] The potential applications they’re discovering away from where they initially thought they’d end up. ·       [09:05] The customer research and tech development that goes into scaling a vertical SaaS company.·       [14:34] They explain the challenge of evangelizing their product to aviation companies.·       [17:50] The guidelines they used to come up with product pricing according to industry standards.·       [21:00] They describe Bluetail’s capital stack, their startup backgrounds, and recent hiring spree.·       [25:38] They share some of their plans geared towards aligning Bluetail in the industry.·       [28:10] Rapid questions with Roberto and Stuart!Memorable Quote:·       “In startup, where you start is never where you end up.”- Stuart [07:52]Connect with Roberto and Stuart:·       Roberto’s LinkedIn: https://www.linkedin.com/in/rguerrieri/·       Stuart LinkedIn: https://www.linkedin.com/in/stuartillian/
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Apr 4, 2023 • 35min

Anthony Kennada of AudiencePlus on Changing B2B Marketing Through Owned Media and First Party Data

Are you leading with value? Where are you sending your audience other than talking to sales and trying the product? Leading with value, which involves building a relationship with your audience and owning the distribution of your content, increases your conversion rate as a B2B company.In this episode of The Capital Stack, we have Anthony Kennada, the co-founder and CEO of AudiencePlus. They’re building software, content, and community to help every company become a media company. We discuss what it means to bring the idea of building thought leadership as a brand in SaaS and producing audience-engaging content.Listen in to learn how AudiencePlus can help you receive your audience’s data and understand the type of content they’re interested in. You will also learn the importance of focusing on creating authentic content as an early-stage startup to build an audience and brand.What You Will Discover:·       [00:00] Intro·       [02:02] Anthony on his career journey and how he’s bringing the idea of building thought leadership as a brand in SaaS.·       [05:31] How to build a relationship with an audience while owning the distribution of your content.·       [08:55] How AudiencePlus can help you receive your audience’s data and understand them. ·       [13:08] How SaaS companies can use AudiencePlus data to create content and engage with their audience.·       [18:06] Examples of B2B companies best in producing content and engaging with their audience.·       [22:37] The value of short-form and long-form content and events in any B2B sales funnel.·       [25:52] How to start creating authentic content as an early-stage startup to build an audience.·       [29:34] The value of partnerships in helping you stand out and accelerate your audience-building efforts.·       [31:08] Rapid questions with Anthony!Memorable Quote:·       “We have a chance to 10x our web conversions by building a relationship with an audience owning the distribution of our content into that audience.”- Anthony [08:17]Connect with Anthony:·       LinkedIn: https://www.linkedin.com/in/akennada/
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Mar 28, 2023 • 26min

Tori Barlow of Allbound on How To Scale a Marketing Motion from $1M-$20M in ARR

What is the best customer acquisition marketing strategy for a B2B startup in the digital era? Optimizing your SEO, doing paid search advertising, and content generation are some ways to market a startup on a budget and achieve ROI.In this episode of The Capital Stack, we have Tori Barlow, VP of Marketing at Allbound, a partner management software that helps companies manage their partner ecosystem. She leads all marketing initiatives including, digital analysis, paid search and SEO, account-based marketing, attribution reporting, and email marketing. We discuss her team’s marketing efforts that saw Allbound achieve significant growth during the pandemic.Listen in to learn how to become your brand’s sales rep by organically connecting with your ideal customer profile and understanding their wants. You will also learn how to identify a partner that aligns with your brand’s values and nurture a relationship with them.What You Will Discover:· [00:00] Intro· [01:48] Tori’s journey in marketing plus her background in DemandGen and digital marketing.· [4:58] How to use SEO, paid ads, and content generation to position your brand as a thought leader in the market.· [9:00] How to become a sales rep for your brand to learn what your ideal customer profile wants.· [11:39] She explains the strategy they used to identify their ideal customer profile.· [14:26] How they explored targeted paid search, top-of-the-funnel marketing, and third-party activity.· [17:48] The process of nurturing a partnership relationship and identifying the right partner.· [22:34] Why she’s looking forward to events and community marketing for the coming year.· [24:07] Random questions with Tori!Memorable Quote:· “SEO is the best investment you can get started with if you have a smaller marketing budget.”- Tori [5:29]Connect with Tori: · LinkedIn: https://www.linkedin.com/in/tori-barlow-17214b45/
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Mar 21, 2023 • 52min

Jon Hunter former CRO of +$18B of ARR on What Leadership Really Looks Like in Downturns.

Do you think of ways you can make your people better as a leader? To build a culture of safety and trust and develop as a leader requires you to exercise high integrity and add value to your people by being a thoughtful servant leader.In this episode of The Capital Stack, we have Jon Hunter, Chief Revenue Officer, Advisor, Coach, and global business leader with expertise in building and growing world-class organizations such as MicroFocus, Computer Associates, and BMC. He specializes in optimizing people, processes and systems to foster, and maintain high-performance cultures.Listen in to learn how to build trust and safety with your people as an early-stage startup. You will also learn how to learn, earn, and return to get out of your comfort zone and continue growing your career. What You Will Discover:·       [00:00] Intro·       [2:02] Jon on finding balance and reconnecting, plus how the concept of hard work in business has changed.·       [10:31] The fundamental principles of succeeding as a leader in tech and venture capital industries.·       [16:49] How to focus on building trust and safety with your people as an early-stage startup.·       [22:35] The qualities you need to be a servant leader who builds people to follow and stay in the long-term.·       [29:49] The qualities you need to manage a team as a front-line manager and how they change as you move up the leadership levels.·       [42:09] How to focus on your intellectual growth and be successful taking on more responsibility.·       [49:00] Random questions with Jon!Memorable Quote:·       “You should segment your career to learn, earn, and return, and if you focus on the learning, you become a subject matter expert.”- Jon [43:22]Connect with Alex:·       Website: https://hunterxlife.com/·       LinkedIn: https://www.linkedin.com/in/jhunter1/
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Mar 14, 2023 • 33min

Sheldon Lewis of Blueprint Equity on Pricing SaaS Companies and the Early Growth Equity Stage of Investing

Are you holding too tight on your equity when looking for deals? Maybe you shouldn’t get too hung up on valuation as an entrepreneur because if you get to a good outcome with the right partner, you will have plenty of money. What you should be doing instead is focusing on getting a partner that’s going to help you optimize your eventual exit.In this episode of The Capital Stack, we have Sheldon Lewis, co-founder and managing partner at Blueprint Equity. He focuses on growth-oriented investments in payment processing, SaaS, internet, franchising, and business services. He explains what it means to be an early growth equity – a hybrid between venture capital and growth equity.Listen in to learn why historical growth and margins are some of the major factors investors look for when considering investing in a company. You will also learn the difference between Multiple on Invested Capital (MOIC) and Internal Rate of Return (IRR) and the advantages of each in investing.What You Will Discover:·       [00:00] Intro·       [1:27] Why Blueprint Equity considers themselves early growth sitting between venture and growth.·       [4:20] How they operate as a minority investor – helping without forcing their opinions.·       [8:15] Why Sheldon would give MOIC a slight advantage over IRR when it comes to ROI.·       [12:41] The factors they consider when valuing companies, which include historical growth and margins.·       [17:00] The importance of focusing on a trustworthy partner that’s going to help you optimize your exit.·       [19:57] The benefits of having a concentrated portfolio for both the entrepreneur and investor.·       [23:35] Blueprint Equity’s investment focus plus their sourcing strategy.·       [28:03] He explains why they focus more on a business’s recent growth than its age.·       [29:50] What it looks like being a general SaaS investor not afraid to try new things.·       [31:05] Sheldon’s excitement about building a team and making great investments in 2023.Memorable Quote:·       “We are probably less focused on how old the business is as a whole and more focused on what the growth has been lately.”- Sheldon [28:04]Connect with Sheldon:LinkedIn: https://www.linkedin.com/in/sheldon-lewis-28274512
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Mar 7, 2023 • 40min

Aaron Oaks on United Pet Care on Search Funds and Disruptive Business Models within Veterinary Care

What does it take to successfully run a pet care startup during a season when everyone wants to be a pet owner? Providing a complimentary product that engages the vet with their client and takes care of pets’ wellness along the way.In this episode of The Capital Stack, we have Aaron Oaks, the Chief Executive Officer at United Pet Care. We discuss the characteristics and skills it takes to become a search fund, plus how United Pet Care partners with a network of veterinary providers and pre-negotiates rates on their behalf.Listen in to learn about the concept of a search fund, the process of becoming a search funder, and the difference between traditional venture capital and search fund. You will also learn how vets can address inefficiencies in the industry by increasing their operating capacity and average transaction.What You Will Discover:·       [00:00] Intro·       [1:38] Aaron on leaving his corporate career to become an entrepreneur and ended up as a search funder.·       [4:43] He explains what an entrepreneur needs to become a search funder.·       [6:40] The soft skills needed when selecting a founder to lead a search fund.·       [9:20] How Aaron was selected as a founder, plus what sponsors look for in a search fund deal.·       [13:07] He explains what United Pet Care does as an HMO for fur babies and how they differ from insurance.·       [19:11] How United Pet Care helps reduce pet owners’ financial burden for their pet’s wellness.·       [21:53] The delicate two-sided market that Aaron has been trying to navigate over the last two years.·       [28:38] Three ways a vet can address the inefficiencies in the veterinary industry.·       [34:28] Why we’ll continue to see individually branded and locally driven strategies in coming years.·       [37:23] Random questions with Aaron!Connect with Aaron:·       Website: https://www.unitedpetcare.com/·       LinkedIn: https://www.linkedin.com/in/aaron-oaks-89479a8/
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Feb 28, 2023 • 25min

Leib Bolel of Grayhawk Capital on the Venture Outlook of 2023

Where should your investment focus for 2023 be? The 2023 market shift is opening up opportunities as it’s no longer a founder-dominated market. Companies and founders will be looking for reasonable valuations to execute capital efficiency.In this episode of The Capital Stack, we have Leib Bolel, Partner at Grayhawk Capital and President at Arizona Israel Technology Alliance. He has over a decade of experience in new business development, startups, marketing, funding acquisition, and general operations management, which is instrumental in building organizations from the ground up. We discuss the upsides and downsides of working at a venture capital and why it is one of the most challenging industries to get into.Listen in to learn why you must be detailed and diligent when going into a deal and not be emotionally attached. You will also learn why you need to look into the people on the board and management before investing in a company.What You Will Discover:·       [00:00] Intro·       [03:20] Leib on the venture opportunities he saw in Arizona and how he joined Grayhawk Capital.·       [06:00] The challenges of joining the venture industry plus the upsides and downsides of working in it.·       [09:20] The work that goes into fundraising plus the benefits of SPIC fund that Grayhawk enjoys.·       [12:03] How the current 2023 market state is creating opportunities for investors.·       [16:30] The importance of taking your time and having clarity when going into a deal.·       [17:52] How to evaluate the people involved in the board and management before investing in a company.·       [21:21] The hesitation expected to happen due to the pending or current recession.·       [22:27] Leib answers some random questions, plus when to expect Fund 4 from Grayhawk Capital.Memorable Quote:·       “Take your time; there’s always going to be another deal.”- Leib [16:30]Connect with Leib:·       LinkedIn: https://www.linkedin.com/in/leibbolel/
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Feb 21, 2023 • 41min

Alex Houghtalin of Access Venture Partners on Thematic Investing Research and Capturing Value as an Early-Stage Company

What is the right way to organize the knowledge you have in your head into a framework as an early-stage company? Putting your vision onto paper is helpful and a great way to capture industry value and acquire power over your customers and suppliers.  In this episode of The Capital Stack, we have Alex Houghtalin, a senior associate at Access Venture Partners. She has deep experience in business strategy research, advisory, and social entrepreneurship. Alex had a career at the Harvard Business School working on business strategy research and advisory alongside Michael Porter, one of the legends in the field. We discuss the creating shared value, strategy, and social entrepreneurship lessons she learned from Michael Porter.Listen in to learn how a senior associate in a venture capital manages their time and what the role entails. You will also learn about the thematic investing strategy and how to create a market map to identify interesting companies in your area of interest.What You Will Discover:·       [00:00] Intro·       [03:53] Alex on her education background, career interests, and experience working with Michael Porter.·       [09:35] How she advanced her career with the social entrepreneurship lessons she learned from Michael Porter.·       [16:00] The difference between academic and strategy exercises in an early-stage company.    ·       [20:00] The role and time management strategy of a senior associate in a venture capital.·       [23:53] The value of thematic investing strategy plus how Access is doing it in tech.·       [29:43] How she does case studies and develops taxonomies for market strategies she’s seeing.·       [35:10] How to understand the pain of the industries you’re mapping by interviewing company leaders.·       [38:00] Random questions with Alex!Memorable Quote:·       “Profit and purpose are not in conflict, there are highly synergistic, and a lot of our business opportunities are solving social needs.”- Alex Houghtalin [11:30]Connect with Alex:·       Website: https://accessvp.com/LinkedIn: https://www.linkedin.com/in/alexandra-houghtalin/
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Feb 14, 2023 • 41min

Tyler Hall of Drivably on Creating Value Through Executive Coaching and Building High Impact Frameworks for Founders

Today I am talking to my friend Tyler Hall, who was a founder turned executive coach. Tyler is obsessed with providing impact and value to founders with high touch coaching frameworks. You can listen to the podcast on YouTube, Apple, and Spotify.Tyler Hall is a highly accomplished CEO coach, recognized for his work with the world's top CEOs. He shares his insights and expertise as the host of the popular Rollercoaster podcast. Tyler is also an advisor to early stage tech companies, helping to guide their growth and success. When he's not in the boardroom or on the mic, Tyler can be found tearing up the racetrack as a skilled motorcycle racer. He balances his passion for business and speed with his most important roles as a loving husband and father to three wonderful children.
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Feb 7, 2023 • 31min

Josh Wagner of In Revenue Capital on Selling Software in 2023 and the Emergence of Partner Led Growth

Josh is a 20 year Sales, Marketing and Channel veteran helping start-ups scale from $0 - $20MM. Ecosystem led growth has been the “cheat code” to growth, tapping into one to many partner relationships to create more scale with less resources. Josh is the Co-Founder and Partner at In Revenue Capital providing founders with Operator-Immersive Capital.  Josh also leads the Revenue team at Rising Cloud, serves as an advisory board member at CRE OneSource, and hosts the Love Selling Hate Sales Podcast.

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