Cloud Returns | A Software Investing Podcast

Our Guest: Edward Robson is the Founder and Chief Investment Officer (CIO) of 2717 Partners, an investment firm focused on technology and technology-enabled businesses. He is an investor known for his approach to capital allocation and long-term investing in software and technology companies.Episode Topics:The story behind 2717 Partners and the “iron sharpens iron” philosophy.Why technology remains a constantly evolving investment category.ROIC and why capital allocation is under-discussed in software.ROICA: return on intangible capital allocation.R&D and sales and marketing as growth CapEx.Why recurring revenue can be viewed like a durable bond.Gross retention, logo retention, and contract renewal rates.Multi-product strategy and why it improves stickiness.AI hype versus proven AI productivity gains.Lessons from RPA, low-code, no-code, and previous technology cycles.How AI may help software companies build more product surface area internally.Why public companies need clear intrinsic value thinking in the AI age.Why there have been fewer software IPOs.How private markets, secondary liquidity, and venture incentives shape IPO timing.What Edward looks for in great CEOs.The importance of self-awareness, capital allocation, and communication.Resources:https://www.linkedin.com/company/2717-partners/ https://geoffreyamoore.com/book/the-gorilla-game/ About Cloud Returns by Cloud Ratings:Cloud Returns covers ALL types of software investing, whether seed, venture capital, growth equity, private equity, debt, and the public markets.Our host - Matt Harney - is active on Twitter @saasletter and writes "SaaSletter", an investing-oriented SaaS newsletter on Substack.https://cloudradio.cloudratings.com/https://twitter.com/SaaSletterhttps://www.saasletter.com/About Cloud Ratings:Cloud Ratings is a customer outcomes-focused, data-driven software research analyst firm. We exist to allow organizations to make more confident, lower-risk software purchasing decisions.Our Cloud Ratings Category Reports combine user reviews with verified vendor data to impartially identify leading software products. Recent report examples include: Subscription Management Software, Session Replay Software, Sales Compensation Software, and Digital Sales Room SoftwareBuilt upon investigative customer interviews, our True ROI Reports quantify and provide 3rd party validation of a software product’s business value.https://cloudratings.com/

Our Guest: Pat McGovern is a Principal at Bowery Capital, an early-stage B2B fund investing primarily at pre-seed. He focuses on vertical AI and writes the newsletter Capital Efficient.Episode Topics:How Bowery approaches pre-seed in 2026 and what “first institutional capital” looks like today.The shift from “SaaS contracts” to outcome-driven and services-driven models.Pat’s vertical AI playbook.Case study on Enata and how voice-first AI gives field sellers time back while improving CRM quality and sales insights.Why more startups may compete directly for industry spend rather than selling tools to incumbents.What Pat wants in founders.The new definition of technical in the AI era.How to run customer pilots well, including shorter timelines, mid-point check-ins, proof-of-value gates, and prioritizing referenceable logos.Resources:https://x.com/pw_mcgovern?lang=en https://www.linkedin.com/in/pwmcgovernhttps://bowerycap.com/ https://capitalefficient.substack.com/ About Cloud Returns by Cloud Ratings:Cloud Returns covers ALL types of software investing, whether seed, venture capital, growth equity, private equity, debt, and the public markets.Our host - Matt Harney - is active on Twitter @saasletter and writes "SaaSletter", an investing-oriented SaaS newsletter on Substack.https://cloudradio.cloudratings.com/https://twitter.com/SaaSletterhttps://www.saasletter.com/About Cloud Ratings:Cloud Ratings is a customer outcomes-focused, data-driven software research analyst firm. We exist to allow organizations to make more confident, lower-risk software purchasing decisions.Our Cloud Ratings Category Reports combine user reviews with verified vendor data to impartially identify leading software products. Recent report examples include: Subscription Management Software, Session Replay Software, Sales Compensation Software, and Digital Sales Room SoftwareBuilt upon investigative customer interviews, our True ROI Reports quantify and provide 3rd party validation of a software product’s business value.https://cloudratings.com/

In this episode, host Matt Harney speaks with Joey Brookhart, Co-Founder of AlphaRepo and a longtime long-short software investor, as Managing Partner and Portfolio Manager of Sandbrook Capital. Joey explains the SaaS metrics that matter most, the overrated ones investors should avoid, and why earnings day volatility often comes down to “bogeys” and positioning rather than guidance. He also introduces AlphaRepo, the Excel-integrated platform he built to track model revisions and portfolio-wide trends, and offers advice for aspiring buy-side analysts.Episode Topics:Joey’s background in long-short investing and the founding of AlphaRepoThe SaaS metrics that matter most: Net New ARR/ACV, sales efficiency, and free cash flow per shareOverrated metrics: NDR and net customer adds when they don’t tie to real driversWhy earnings day reactions are driven by “bogeys” and positioning gamesForecasting rigor: buy-side models vs. public company guidanceCareer advice: “Get at bats” with pitches and always start with primary documentsThe role of AI in buy-side workflows — an opportunity, not a threatMemorable Quote:On overrated metrics: “Anything that’s really backward-looking, or doesn’t tie to the drivers of the business, is noise.”Resources:AlphaRepoJoey Brookhart on LinkedInJoey on Twitter / X: @SaasquatchC

Our Guests: Marissa Moore, and Taku Murahwi of OMERS Ventures, an early-stage venture capital firm investing in Series A-C companies with a first cheque size between $5-25M. Episode Topics:OMERS Venture’s investment criteria.Type of founders Marissa and Taku prefer.How does OMERS Ventures conduct due diligence on a company founder?Overview of Marissa’s “The Green Room”, a “safe space for founders to practice their pitch, risk-free, in front of current investors and subject matter experts.”Marissa’s advice for how founders can improve their pitches.Deep dive into the Eight Core Factors in OMERS Ventures' AI Deep Dive Report.How does unstructured and industry-specific data affect AI’s effectiveness?Marissa’s insights and strategies from successful companies to gain the trust of their customers.The rationale behind the degree of high-stakes decision-making factor.How long it will take for a AI-native company to move from seed funding to Series A, factoring in the development timelines needed to refine an AI product and scale?Is the Net Promoter Score bar higher for an AI company than a traditional software company?Which industries are more or less suitable for vertical AI solutions based on the Vertical AI Deep Dive Report?Great habits Marissa and Taku learned from someone in OMERS Ventures portfolio.Resources:OMERS Ventures Vertical AI Report: https://airtable.com/appcfwQFbRedHquqo/paghteBojIXj9d72g/form About Cloud Returns by Cloud Ratings:Cloud Returns covers ALL types of software investing, whether seed, venture capital, growth equity, private equity, debt, and the public markets.Our host - Matt Harney - is active on Twitter @saasletter and writes "SaaSletter", an investing-oriented SaaS newsletter on Substack.https://cloudradio.cloudratings.com/https://twitter.com/SaaSletterhttps://www.saasletter.com/About Cloud Ratings:Cloud Ratings is a customer outcomes-focused, data-driven software research analyst firm. We exist to allow organizations to make more confident, lower-risk software purchasing decisions.Our Cloud Ratings Category Reports combine user reviews with verified vendor data to impartially identify leading software products. Recent report examples include: Board Management Software, Account-Based Marketing Software, Cap Table + Equity Management Software, Lead Routing Software, and Sales Training + Onboarding Software.Built upon investigative customer interviews, our True ROI Reports quantify and provide 3rd party validation of a software product’s business value.https://cloudratings.com/

Our Guest: Diamond Innabi is a Principal at Software Equity Group (SEG), a boutique M&A advisory firm headquartered in San Diego that focuses on B2B vertically focused software and SaaS companies.Episode Topics:Understanding the full cycle - from prep to closing - of selling your company.When should CEOs engage with an investment banker or consider an M&A path?Common mistakes that founders, CEOs, and boards make during the M&A process.Diamond's advice to founders who are interfacing with potential acquirers.Overview of SEG’s 20 Factor Valuation Scorecard.Difference between strategic buyers and private equity firms in terms of acquisition criteria. Diamond elaborates on the 2023 M&A Report: “The higher-than-usual volume of low multiple deals is a result of from negative transaction catalysts like evaporating cash runway, challenging debt dynamics, competitive concerns, or investors opting to exit their lower-performing assets to focus on high performers.”Factors influencing premium valuations for select companies.Resources:https://softwareequity.com/research/ https://softwareequity.com/company-valuation-formula/https://softwareequity.com/research/saas-ma-buyers-perspectivesAbout Cloud Returns by Cloud Ratings:Cloud Returns covers ALL types of software investing, whether seed, venture capital, growth equity, private equity, debt, and the public markets.Our host - Matt Harney - is active on Twitter @saasletter and writes "SaaSletter", an investing-oriented SaaS newsletter on Substack.https://cloudradio.cloudratings.com/https://twitter.com/SaaSletterhttps://www.saasletter.com/About Cloud Ratings:Cloud Ratings is a customer outcomes-focused, data-driven software research analyst firm. We exist to allow organizations to make more confident, lower-risk software purchasing decisions.Our Cloud Ratings Category Reports combine user reviews with verified vendor data to impartially identify leading software products. Recent report examples include: Board Management Software, Account-Based Marketing Software, Cap Table + Equity Management Software, Lead Routing Software, and Sales Training + Onboarding Software.Built upon investigative customer interviews, our True ROI Reports quantify and provide 3rd party validation of a software product’s business value.https://cloudratings.com/

Our Guest: Paul Stansik is the Private Equity Operating Partner at ParkerGale Capital, a B2B focused private equity firm, buying profitable technology companies from founders.Episode Topics:Paul and PartnerGale Capital's investment criteria.What does an operating partner do?A brief overview of Paul's weekly sales playbook at PartnerGale Capital.Approach to gaining a deeper understanding of a business's dynamics.Paul elaborates: "Always scrubbing the pipeline means never scrubbing the pipeline."Assessing the “sales machine” of a target investment during due diligence..Paul’s view on the impact of AI on sales and marketing.An overview of ParkerGale's hiring playbook.Realities and challenges of building teams in the middle market.Resources:Paul Stansik’s Substack: https://hellooperator.substack.com/The Weekly Sales Metrics Playbook Hiring Playbook Slides: How We Hire At ParkerGale "What CEOs Should Expect From Their Sales Leader" "AI’s Impact on Sales + Marketing" About Cloud Returns by Cloud Ratings:Cloud Returns covers ALL types of software investing, whether seed, venture capital, growth equity, private equity, debt, and the public markets.Our host - Matt Harney - is active on Twitter @saasletter and writes "SaaSletter", an investing-oriented SaaS newsletter on Substack.https://cloudradio.cloudratings.com/https://twitter.com/SaaSletterhttps://www.saasletter.com/About Cloud Ratings:Cloud Ratings is a customer outcomes-focused, data-driven software research analyst firm. We exist to allow organizations to make more confident, lower-risk software purchasing decisions.Our Cloud Ratings Category Reports combine user reviews with verified vendor data to impartially identify leading software products. Recent report examples include: Board Management Software, Account-Based Marketing Software, Cap Table + Equity Management Software, Lead Routing Software, and Sales Training + Onboarding Software.Built upon investigative customer interviews, our True ROI Reports quantify and provide 3rd party validation of a software product’s business value.https://cloudratings.com/

Our Guest: Dave Yuan is the Founder of Tidemark, a growth equity firm focused on helping companies scale. With over 20 years of experience, Dave has invested in twelve companies that have gone public, eight that have been acquired.Episode Topics:Dave and Tidemark’s investment criteria.Ideal qualities for vSaaS founders.Dave's viewpoints on overspending in R&D, product risk, and product development in vertical SaaS.What does good multi-product sequencing look like?Is AI an opportunity, neutral, or a threat in vertical SaaS? The supply/demand imbalance between private investors and scaled vertical SaaS companies.A framework for determining when to raise more capital or pursue a capital-efficient path.What SaaS company does Dave admire the most?Dave’s learnings from starting a new fund.Resources:Tidemark Vertical SaaS Knowledge Project: https://www.tidemarkcap.com/vskpTidemark 2024 Vertical SaaS Benchmark Survey: https://www.surveymonkey.com/r/5CFVSHQAbout Cloud Returns by Cloud Ratings:Cloud Returns covers ALL types of software investing, whether seed, venture capital, growth equity, private equity, debt, and the public markets.Our host - Matt Harney - is active on Twitter @saasletter and writes "SaaSletter", an investing-oriented SaaS newsletter on Substack.https://cloudradio.cloudratings.com/https://twitter.com/SaaSletterhttps://www.saasletter.com/About Cloud Ratings:Cloud Ratings is a customer outcomes-focused, data-driven software research analyst firm. We exist to allow organizations to make more confident, lower-risk software purchasing decisions.Our Cloud Ratings Category Reports combine user reviews with verified vendor data to impartially identify leading software products. Recent report examples include: Board Management Software, Account-Based Marketing Software, Cap Table + Equity Management Software, Lead Routing Software, and Sales Training + Onboarding Software.Built upon investigative customer interviews, our True ROI Reports quantify and provide 3rd party validation of a software product’s business value.https://cloudratings.com/

Our Guest: Akash Bajwa is an investor in fintech and B2B SaaS at Earlybird Venture Capital, a European venture capital firm with 2 billion Euros in assets under management (AUM).Episode Topics:Akash and Earlybird’s investment criteria Areas in early-stage native AI that Akash and Earlybird are excited aboutAkash discusses the unique skill sets needed for native AI founders.Is building an AI-focused business similar to the well-established SaaS playbook?Akash’s views on investor returns if gross margins decrease to 50% in AI-driven software.How are software pricing models going to evolve in an AI world?Methods for assessing a founder's execution ability during early-stage fundraising.Akash’s views on vertical software and implications of AI lowering barriers to software creation.Akash's view on AI's capital intensity +  its implications of this for investors.Resources:https://substack.com/@akashbajwahttps://www.earlybird.com/About Cloud Returns by Cloud Ratings:Cloud Returns covers ALL types of software investing, whether seed, venture capital, growth equity, private equity, debt, and the public markets.Our host - Matt Harney - is active on Twitter @saasletter and writes "SaaSletter", an investing-oriented SaaS newsletter on Substack.https://cloudradio.cloudratings.com/https://twitter.com/SaaSletterhttps://www.saasletter.com/About Cloud Ratings:Cloud Ratings is a customer outcomes-focused, data-driven software research analyst firm. We exist to allow organizations to make more confident, lower-risk software purchasing decisions.Our Cloud Ratings Category Reports combine user reviews with verified vendor data to impartially identify leading software products. Recent report examples include: Board Management Software, Account-Based Marketing Software, Cap Table + Equity Management Software, Lead Routing Software, and Sales Training + Onboarding Software.Built upon investigative customer interviews, our True ROI Reports quantify and provide 3rd party validation of a software product’s business value.https://cloudratings.com/

Our Guest: Nick Tippman, former Chief Marketing Officer at Greenlight Guru, a category-leading provider of regulatory software for the MedTech vertical. He is now an angel investor, investing in exceptional Vertical/SMB SaaS, AI, Fintech, and B2B Marketplace founders and companies at the pre-seed/seed stage alongside other leading investors.Episode Topics:Nick’s current investment criteria for a vertical SaaS company.Nick’s minimum TAM + how he looks at take rates.How important are fintech and payment opportunities in evaluating vertical software markets?How embedded APIs - like embedding payroll into your app - are changing opportunity sets for seed-stage vertical SaaSWhat constitutes founder market fit?Nick’s advice on effectively demonstrating founder-market fit in a pitch deck.Nick’s views on the increased venture capital flow into niche vertical markets.The impact of Generative AI in breaking through to categories that have been resistant to digital transformationIs AI an opportunity, neutral, or a threat? Eli Dukes Question: What's the primary challenge in vertical SaaS: Is it GTM or product? Why?How to assess founders and their teams' product management skills in this changing landscape?Understanding operator funds + Nick’s perspective as a Limited Partner (LP) in 11 funds.Nick’s recommendations and tactical advice for potential emerging managers.Resources:Eli Dukes Vertical SaaS Substack - https://verticalized.co/Nick’s Google Doc - “Ultimate List of 37+ VC & PE Firm Theses & Market Updates on Vertical SaaS”About Cloud Returns by Cloud Ratings:Cloud Returns covers ALL types of software investing, whether seed, venture capital, growth equity, private equity, debt, and the public markets.Our host - Matt Harney - is active on Twitter @saasletter and writes "SaaSletter", an investing-oriented SaaS newsletter on Substack.https://cloudradio.cloudratings.com/https://twitter.com/SaaSletterhttps://www.saasletter.com/About Cloud Ratings:Cloud Ratings is a customer outcomes-focused, data-driven software research analyst firm. We exist to allow organizations to make more confident, lower-risk software purchasing decisions.Our Cloud Ratings Category Reports combine user reviews with verified vendor data to impartially identify leading software products. Recent report examples include: Board Management Software, Account-Based Marketing Software, Cap Table + Equity Management Software, Lead Routing Software, and Sales Training + Onboarding Software.Built upon investigative customer interviews, our True ROI Reports quantify and provide 3rd party validation of a software product’s business value.https://cloudratings.com/

Our Guest: Brian Parks is the Co-Founder and CEO of Bigfoot Capital, a non-venture debt lending firm, that provides growth and bridge debt facilities to SaaS companies with $2+ million in annual recurring revenue. Episode Topics:Current access to capital environment - “2/3 of equity investors and lenders expect to be more active over the next 12 months”Disconnects after the failure of Silicon Valley Bank (SVB)Unique financing opportunities after disruptions like SVBWhat are the table stakes - like data rooms and timelines - for non-venture-backed software company founders when raising debt capital?Bigfoot’s core loan investment criteria (loan size, typical revenue size, and facility size)Brian expounds on “being frivolous with equity” quote - “I'm anti-frivolity with equity and think a lot of people are extremely frivolous with their equity, selling too much of their company too early."Brian’s perspective on the changing dynamics of whether to bootstrap + the increasing presence of VC in typically bootstrapped categories Understanding Bigfoot’s underwriting - lending three to six times MRR - from a credit support perspectiveThe absence of equity warrants in Bigfoot's lending modelResources:https://bigfootcap.com/https://bigfootcapital.substack.com/ https://bigfootcapital.substack.com/p/capital-provider-sentiment-survey-17dhttps://calendly.com/bigfootAbout Cloud Returns by Cloud Ratings:Cloud Returns covers ALL types of software investing, whether seed, venture capital, growth equity, private equity, debt, and the public markets.Our host - Matt Harney - is active on Twitter @saasletter and writes "SaaSletter", an investing-oriented SaaS newsletter on Substack.https://cloudradio.cloudratings.com/https://twitter.com/SaaSletterhttps://www.saasletter.com/About Cloud Ratings:Cloud Ratings is a customer outcomes-focused, data-driven software research analyst firm. We exist to allow organizations to make more confident, lower-risk software purchasing decisions.Our Cloud Ratings Category Reports combine user reviews with verified vendor data to impartially identify leading software products. Recent report examples include: Sales Engagement Software, Sales Conversation Intelligence Software, Sales Compensation Software, and Digital Sales Room SoftwareBuilt upon investigative customer interviews, our True ROI Reports quantify and provide 3rd party validation of a software product’s business value.https://cloudratings.com/