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Father and son team John and Tyler Richards — veteran entrepreneurs, venture investors, mentors, and educators — discuss all things entrepreneurship and venture capital.
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Devin Shurtleff: Overcoming Challenges, Strategic Shifts, and Lessons from a CEO’s Leadership Legacy
13 MAR 2025 · In this episode, we welcome Devin Shirtle, the newly appointed CEO and co-founder of Opinion, a company that has been revolutionizing feedback and review automation for multifamily residential complexes for the past eight years. Join us as Devin shares the inspiring journey of Opinion, from its humble beginnings to its current success, highlighting key strategies in financial management, customer retention, and leadership. The conversation also delves into the personal impact of losing a co-founder and how the company has persevered through challenges.
(00:00:00) - Welcome to the Startup Ignition podcast with guest Devin Shirtle, CEO of Opinion.
(00:04:03) - Icebreaker game: Devin answers fun This or That questions.
(00:14:02) - Devin explains Opinion’s mission to automate feedback for multifamily residential complexes.
(00:16:41) - The inspiring founding story of Opinion, from a simple idea to a thriving business.
(00:28:37) - How Opinion strategically shifted to focus on the multifamily residential sector.
(00:33:15) - Devin shares crucial financial strategies for entrepreneurs, including managing cash flow and ARR.
(00:39:16) - Reflecting on the CEO role and honoring the legacy of the late Justin Bingham.
(00:53:49) - The story of how Opinion’s team rallied together after Justin’s passing, showcasing resilience.
(00:59:29) - Devin discusses exciting future plans for Opinion, including growth and acquisitions.
(01:05:37) - Personal reflections from Devin on life, leadership, and moving forward.
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#Entrepreneurship
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#DevinShirtle
#Opinion
#FeedbackAutomation
#MultifamilyResidential
#FinancialStrategies
#Leadership
#Resilience
#CustomerRetention
#PersonalGrowth
Transcribed
6 MAR 2025 · In this episode, we welcome John Pestana, a seasoned entrepreneur best known for co-founding Omniture, a web analytics company acquired by Adobe for $1.8 billion. Currently, John serves as CEO of ObservePoint, a leading data governance company, and as chairman of the board for Libertas Institute, advocating for liberty and free market principles. His induction into the Silicon Slopes Hall of Fame in 2022 underscores his significant contributions to Utah's tech landscape.
(00:00:00) - The problem with enterprise sales companies.
(00:01:21) - Welcome to the Startup Ignition podcast with guest John Pestana (JP).
(00:02:03) - JP's background, co-founding Omniture and current role at ObservePoint.
(00:02:48) - JP's impact on Utah's tech scene.
(00:04:03) - Icebreaker game: Would you rather?
(00:04:54) - Would you rather raise $100 million VC round but lose control, or bootstrap and grow 10x slower?
(00:05:56) - Raising money is like getting a loan on your house.
(00:06:35) - Would you rather relive the dot com crash or the housing crash with what you know today?
(00:07:54) - JP owns only one stock: Domo.
(00:08:06) - Would you rather work on a startup solving a huge problem or build a company in a boring industry and make millions quickly?
(00:09:23) - Would you rather go back in time and change one decision or fast forward to see the future of your next venture?
(00:10:51) - JP's history and relationship with the hosts.
(00:11:46) - JP's start in tech: Lynn Mkel's class and recruiting help.
(00:12:02) - JP's Mormon mission in Brazil and decision to switch to business and computers.
(00:13:21) - Josh James joins JP's group project.
(00:14:19) - Selling wedding presents to start JP Graphics.
(00:15:17) - Josh joins JP to sell websites.
(00:15:58) - Measuring website performance with WebTrends.
(00:16:32) - Creating a web-based analytics company.
(00:16:51) - Jeremy Young's idea and the inspiration for Superstats.
(00:17:55) - Matt Heaton's other ventures and JP's focus on stats.
(00:18:18) - WebTrends vs. Superstats: server logs vs. one pixel.
(00:19:55) - Moving from JP Graphics to JP Interactive to Superstats.
(00:20:10) - Making money while sleeping: Script Search.
(00:21:16) - Exchanging stats for a banner on your website.
(00:22:11) - Flipping to a paid service during the Internet crash.
(00:23:00) - Superstats before mycomputer.com.
(00:23:10) - Investing in Superstats.
(00:23:57) - Focusing on enterprise analytics.
(00:24:50) - Switching to a paid model after the Internet crash.
(00:26:09) - The sale of the company that fell through.
(00:27:58) - Letting go of 70% of staff.
(00:29:17) - Paying severance years later.
(00:30:36) - Acquisition of Omniture to Adobe.
(00:31:20) - Exciting things that were happening when switching to enterprise.
(00:32:55) - Enterprise sales is super hard.
(00:33:37) - Venture fund and SaaS subscriptions.
(00:34:57) - Creating value and a good product.
(00:35:02) - Transition at ObservePoint: enterprise sales to PLG.
(00:36:19) - True engagement with renewal.
(00:37:53) - Successful PLG companies adding an enterprise button.
(00:39:13) - Acquisition and going public.
(00:41:39) - Stock prices going up.
(00:41:46) - Acquiring Website Story and Visual Sciences.
(00:42:03) - JP's retirement.
(00:44:26) - How much time it actually takes.
(00:44:46) - JP's accomplishments.
(00:45:37) - Starting Silicon Slopes.
(00:46:01) - Advancing personal freedoms with Libertas.
(00:46:15) - Helping young entrepreneurs.
(00:47:38) - Personal initiatives and belief system.
(00:48:48) - Funny story involving John and Google Fiber.
(00:50:55) - Take on the current presidency.
(00:51:43) - Anti patent and protectionism.
(00:53:49) - Elon Musk and the DOJ initiative.
(00:56:12) - Common sense legislation on environmentalism.
(00:57:46) - Tariffs and negotiation leverage.
(00:58:47) - Nuclear power as a solution.
(01:00:00) - The need for stability.
(01:00:46) - Sandbox legislation in Utah.
(01:02:07) - Bitcoin and cryptocurrencies.
(01:02:50) - Favorite place to visit: India.
(01:05:03) - Thank you to John.
(01:05:37) - PLG process in the software world mixed with enterprise sales.
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#Entrepreneurship
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#JohnPastanaInterview
#Omniture
#WebAnalytics
#DataGovernance
#ObservePoint
#LibertasInstitute
#SiliconSlopesHallOfFame
#BootstrappingVsVCFunding
#DotComCrash
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#EnterpriseSales
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#SaaSBusinessModel
#GoogleFiber
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Transcribed
27 FEB 2025 · In this episode, we speak with Shane Murphy, the CEO and co-founder of Boostly. Shane shares his transition from a successful sales career to the world of entrepreneurship, detailing his journey of launching an SMS marketing startup for restaurants. He emphasizes key strategies such as validating business ideas, leveraging mentorship, adapting to market needs through flexible pricing and product offerings, and the critical importance of building a strong, capable team.
(00:00:00) - Icebreaker game: Never have I ever
(00:00:59) - Introducing Shane Murphy from Boostly
(00:01:33) - Boostly's $22 million Series A announcement
(00:02:34) - Welcoming Shane to the Startup Ignition podcast
(00:06:49) - Diving into Shane's background and history
(00:07:55) - Shane's journey to becoming a sales leader
(00:08:52) - From music major to sales
(00:10:09) - First exposure to sales as an SDR
(00:10:48) - Joining American Healthcare Lending
(00:11:53) - Assuming a founder-like role
(00:12:42) - Investing in American Healthcare Lending
(00:13:16) - Preparing to be an entrepreneur
(00:13:57) - Transitioning to Jolt
(00:14:29) - Scaling sales at Jolt
(00:16:05) - Discovering Startup Ignition
(00:16:46) - Attending the Startup Ignition boot camp
(00:18:35) - Jotting down ideas and problems to solve
(00:19:32) - Gaining confidence to start a company
(00:20:10) - Being a meticulous lean startup follower
(00:21:05) - Advice on approaching a startup idea
(00:22:28) - Pouring everything into Jolt
(00:22:58) - Preparing financially to go all in
(00:23:53) - Validating while working for someone else
(00:24:19) - Getting the push to quit and start a company
(00:25:07) - Discussions surrounding quitting
(00:25:42) - Feeling nervous and getting a sign
(00:26:19) - Validating the startup idea
(00:27:11) - Starting cold calling and setting appointments
(00:27:43) - First hypothesis for a business model
(00:28:55) - The classic marketplace chicken and egg concept
(00:29:34) - Landing on a direct online ordering solution
(00:30:24) - Timeline from quitting to landing on the third or fourth idea
(00:31:13) - Pre-selling as part of validation
(00:31:48) - Only a founder can do what Shane did
(00:32:28) - Testing the Chowow hypothesis
(00:33:18) - Showing customers PowerPoint slides
(00:34:04) - Pitching to Chowow customers
(00:34:50) - Hunting for a co-founder
(00:36:16) - John's network and finding Mikey
(00:37:35) - Mikey's background and desire for a business co-founder
(00:38:35) - Mikey checking every box
(00:39:32) - Serendipity, timing, and being easy to work with
(00:40:02) - Mikey's business acumen
(00:40:19) - Working together at the startup building
(00:40:46) - Incorporating the company
(00:41:15) - Launching the MVP
(00:41:59) - Launching to pre-sold customers
(00:42:26) - Realizing the need to pivot
(00:43:14) - Brute force sales and product market fit challenges
(00:43:58) - Pivoting and focusing on marketing tools
(00:44:53) - Leaning into the value proposition
(00:45:27) - Everything's a hypothesis until validated
(00:45:48) - The accelerated process and quickness
(00:46:27) - Going to the International Pizza Expo
(00:47:09) - Focusing on retention and doubling revenue
(00:47:34) - Restaurants shutting down due to the pandemic
(00:48:06) - Validating additional products during the pandemic
(00:49:04) - Restarting with a new pricing model
(00:49:44) - Going through Y Combinator
(00:49:54) - SMS marketing for restaurants
(00:50:30) - Raising capital at the end of Y Combinator
(00:51:15) - Marketing tools for restaurants
(00:51:26) - Closing a seed round of capital
(00:52:07) - Trestle partners leading the seed round
(00:52:25) - Peak Span Capital leading the Series A
(00:53:06) - Trestle's investment stage
(00:53:47) - Closing the seed round in May 2024
(00:54:16) - Peak Span reaching out and structuring a deal
(00:55:12) - A preemptive series A
(00:56:28) - Are you happy?
(00:57:19) - Shane's a great guy who assimilated information
(00:57:59) - Aligning with methodologies
(00:58:11) - Parting wisdom and advice
(00:59:28) - Fundraising takes care of itself if you build a good business
(01:00:34) - Wrapping up the podcast
(01:00:50) - Staying up to date with Boostly
(01:01:14) - Boostly's been around for eight years
(01:01:45) - Shane's a good person
(01:01:57) - Success comes from solving real-world problems
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#Startup #Entrepreneurship #SMSMarketing #RestaurantMarketing #BusinessValidation #PreSales #ProductMarketFit #TeamBuilding #Fundraising #VentureCapital #StartupAccelerator #YCombinator #Adaptability #CustomerFocus #LeanStartup #ShaneMurphy #Boostly #Mentorship #PricingModels #SalesStrategy
Transcribed
21 FEB 2025 · In this episode, we discuss current fundraising trends, the importance of sustainable business models, and key attributes of fundable startups, offering advice on how to navigate the venture capital landscape.
(00:00:00) - An email firing
(00:01:29) - Podcast introduction
(00:01:51) - Icebreaker: Who's more likely?
(00:02:21) - Investing in a terrible idea
(00:02:54) - Pitching an existing startup idea
(00:03:29) - Ignoring Excel for gut decisions
(00:03:56) - Starting and exiting a billion-dollar company
(00:06:13) - Launching a startup without validation
(00:06:54) - Firing someone via email
(00:07:59) - Meeting with an investor just because they're famous
(00:09:19) - Making more pivots in a startup
(00:10:13) - Running a company that burns $10 million before making $1 of revenue
(00:10:55) - Google stories
(00:12:48) - Fundraising as a hot topic
(00:14:13) - Raising money doesn't solve all your problems
(00:16:09) - Diving into fundraising
(00:16:39) - Forbes article: Why 2025 Looks Like a Big Year for Venture Capital
(00:17:51) - Startup Ignition Ventures' thesis on building in venture
(00:19:45) - Feedback on sustainable business models
(00:20:37) - The father of lean startup, Steve Blank
(00:21:39) - When to sell assets built up in venture
(00:22:47) - Wall Street Journal article: Venture Capital needs a new math
(00:23:45) - Funding a company that became a billion dollar unicorn
(00:24:08) - High valuation early on in your startup
(00:25:40) - Numbers and examples of high valuation
(00:27:26) - $30 million valuation warrants some form of revenue
(00:28:45) - Fundraise the capital that you actually truly need
(00:29:15) - The cycle of trough and the valley
(00:30:05) - Analyzing a deal
(00:31:21) - What we look for
(00:32:24) - Aspects and attributes of a fundable project
(00:32:59) - SaaS business
(00:33:14) - The founder
(00:33:28) - Primary, secondary and tertiary founders
(00:34:13) - Detail oriented, passionate, thorough, thoughtful
(00:35:32) - Industry experience
(00:36:22) - Coachable, resourceful, adaptable, smart
(00:36:35) - Market opportunity
(00:37:19) - Total addressable market
(00:37:45) - Timing of the opportunity
(00:38:23) - Business model
(00:38:34) - Revenue potential
(00:39:40) - Traction and validation
(00:41:31) - Monthly recurring revenue
(00:42:07) - Wasted energy, resources, time and money around building startups
(00:43:32) - Societal benefit
(00:44:14) - Lean Startup
(00:46:05) - Attributes that we look for in an investable project
(00:47:09) - Scalable companies
(00:48:06) - Online community questions
(00:48:32) - Taking money from an investor you don't fully trust
(00:51:55) - Investing in a great team with a bad idea or a bad team with a great idea
(00:52:23) - Mistakes founders make in a pitch meeting
(00:55:13) - Meeting investors without warm intros
(00:57:23) - Networking and referrals
(00:58:46) - The importance of universities
(01:00:07) - Investors are changing their strategy
(01:00:47) - Thank you and goodbye
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#BusinessModelValidation
Transcribed
14 FEB 2025 · In this episode, we explore the evolving entrepreneurial landscape heading into 2025, covering the impact of AI, macroeconomic cycles, venture capital trends, and foundational principles like founder-market fit and business model validation.
(00:00:00) - Welcome back to Startup Ignition for episode two.
(00:01:24) - Father-son icebreaker: startup terminology.
(00:02:01) - Defining "Dulu" in startup lingo.
(00:02:28) - Defining "Let them cook" in startup lingo.
(00:02:56) - Defining "Riz" in startup lingo.
(00:03:49) - Defining "Brainrot" in startup lingo.
(00:04:13) - Old school vs. new school: the changing landscape for entrepreneurs in 2025.
(00:05:07) - Multi-decade look at venture scalability.
(00:06:22) - AI's impact on reducing startup costs.
(00:07:51) - AI as a generational innovation.
(00:08:53) - Macroeconomic effects on venture and startups.
(00:09:56) - Experiencing an economic downturn.
(00:11:31) - Feeling the abnormality of 2020-2021.
(00:12:18) - Being aware of the macroeconomic cycle.
(00:13:23) - The trough of an economic cycle as a fantastic time to start a company.
(00:15:27) - Cautions for new thinking in 2025.
(00:16:15) - Sam Altman's view on entrepreneurship.
(00:17:11) - The changing VC landscape in 2025.
(00:18:25) - VC's exuberance and pessimism cycles.
(00:20:08) - Advice for companies that have struggled but reached a certain revenue.
(00:21:06) - What's staying the same: foundational principles.
(00:21:30) - The importance of a great idea and business opportunity.
(00:22:49) - Defining a business model.
(00:23:13) - Validating hypothesized business models.
(00:24:41) - Traction and revenue as cash kings.
(00:25:13) - Revenue cures all ills.
(00:27:14) - Strategies that are now ill advice.
(00:28:07) - Focusing on problem-hunting when building a startup.
(00:29:18) - The importance of founder market fit.
(00:29:57) - War story: immense founder market fit.
(00:33:17) - The importance of execution.
(00:33:42) - Big tech leaders at the inauguration.
(00:35:11) - The new administration is pro business.
(00:36:21) - Renaissance in entrepreneurship.
(00:37:13) - The Stargate proposal for AI infrastructure leadership.
(00:38:18) - Deregulation and its impact on small businesses.
(00:39:02) - Regulations on small businesses.
(00:40:55) - Small business vs. scalable venture.
(00:41:51) - Pre-seed AI fundraises and Startup Ignition Ventures' stance.
(00:43:47) - The lemmings approach to investing in AI.
(00:45:57) - Capital efficiency and enhanced features coming from AI.
(00:46:33) - Products attacking a specific workflow or vertical.
(00:50:22) - VC and fundraising.
(00:50:36) - Entrepreneurs choosing to bootstrap.
(00:52:14) - When is the right time to fundraise vs. bootstrap?
(00:54:40) - The importance of zero churn.
(00:56:19) - Wrapping up another great episode.
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Transcribed
7 FEB 2025 · 00:00 Introduction
01:06 Startup Insights
02:31 Early Experiences
04:04 Experiences at Google
05:03 Startup Ignition
06:04 Startup Challenges
07:34 Lean Startup Principles
08:10 Validation Importance
11:13 Success Stories
13:28 Scalable Ventures
34:18 Investing Criteria
40:23 AI Trends
54:20 Economic Cycles
56:40 Conclusion
Join our online academy for free:
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#StartupIgnition #StartupAdvice #LeanStartup #EntrepreneurshipInsights #VentureInvesting #ValidatedBusinessModel #SiliconSlopes #B2BSaaS #StartupSuccessStories #EntrepreneurialEcosystem #FatherSonDuo #StartupEcosystem #StartupLessons #AIImpactStartups #BusinessValidation #ScalableVentures
Father and son team John and Tyler Richards — veteran entrepreneurs, venture investors, mentors, and educators — discuss all things entrepreneurship and venture capital.
Information
| Author | Startup Ignition |
| Organization | Startup Ignition |
| Categories | Entrepreneurship , Business , Management |
| Website | startupignition.com |
| podcast@startupignition.com |
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