Build & Break Through

R. Hunter Harris
  • 5.0 (2)
  • Entrepreneurship

Most startups don't die from bad ideas. They die from the same handful of mistakes, made over and over, that nobody warned them about. Build and Break Through is Hunter Harris - fractional CPTO, advisor, and four-exit operator - in real conversations with the founders, builders, and operators who've lived it and are living it. The wins, the wrecks, and the hard-won lessons in between. Hunter's spent years watching the same questions sink good companies. This show takes the answers out of the boardroom and into yours - give-first, no fluff - so founders can ship, survive, scale, and succeed.

  1. 1d ago

    Control Before Thrust: Making AI Work with Josh Colter

    What would help your customers more: another round of faster AI output, or a better way to see what you're building? Josh Colter, the majority owner of Cardboard, has put a lot of thought into that question. He bought the company with a bet on AI and has been combining story maps with detailed instructions so he can see the big picture while the models work through the details. His comparison comes from the Wright brothers. He says "they thought about control first." A bigger engine is useful once you can steer. Josh applies that idea to building software: make the work visible, understand the customer behavior you're trying to change, and keep releases small enough to inspect. We talk about the difference between having AI drive and learning to operate it yourself, why a long specification can hide something a human needs to see, and how Josh planned and shipped dark mode in three days after finding years of requests from users of a competing product. Useful questions from the conversation Can you see the work clearly enough to tell where it's going? Can the people building it understand the plan as readily as the AI can? What customer request are you trying to meet, and how will you check the result? Chapters 00:00 Control before thrust 00:45 Show intro 00:53 Meet Josh Colter 01:26 Buying Cardboard and betting on AI 02:46 Chauffeurs and airmen 08:47 Why a bigger engine needs control 11:05 Make the work visible 15:20 Story maps, specifications and human understanding 20:32 Planning and shipping dark mode 25:26 Checking what you've actually built 26:35 Where to find Josh and Cardboard

  2. Sep 27

    Brandon Valentine: Unit Economics - Why Founders Can't Raise Capital Without Them

    In this episode, Brandon Valentine, a CPA and the founder of Valentine Advisory Group, explains why a founder who can't speak to their unit economics can't raise capital: lenders and investors want to understand how the company makes money and how they get their capital back. He breaks down what goes into the numbers (cost of goods sold, operating expenses and a price the market will pay), why pricing starts with market research and the problem you solve for the customer, and how a three statement financial model turns "I want money because my idea is very good" into a specific ask backed by numbers. Hunter adds why bad unit economics get worse with growth: lose money on one widget and you lose more on a thousand. They also cover finance tools versus finance expertise, how to vet a CPA, and how AI is changing accounting work, including why it still depends on good data going in. Founders preparing to raise will learn which numbers to get right before the pitch. Chapters 00:00 Asking for capital with numbers, not belief 00:37 Introducing Brandon Valentine and Valentine Advisory Group 01:11 Where founders should start: unit economics 03:40 Why you can't raise without your unit economics 04:53 Labor, operating expenses and early foundations 06:55 Bad unit economics lose more as you scale 07:40 Pricing, freemium and market research 10:16 Pricing to the problem you solve 12:50 The three statement model and the capital ask 15:03 Finance tools versus finance expertise 16:33 How to find and vet a CPA 18:07 How AI is changing accounting and finance 23:02 Where AI goes wrong: bad data in, bad data out 24:23 Where to find Brandon Host: R. Hunter Harris https://www.linkedin.com/in/rhunterharris/ Guest: Brandon Valentine Brandon is a CPA from Atlanta and the founder of Valentine Advisory Group. He helps people buy and sell businesses in the lower middle market and helps founders and small business owners build their accounting and finance foundations. https://www.linkedin.com/in/brandon-valentine-cpa https://valentineadvisorygroup.com/ By Hunter Software Consulting https://huntersoftwareconsulting.com/

  3. Sep 20

    Kevin Callahan: Startup Fundraising - What a 1,000-Hour Raise Actually Takes

    In this episode, Kevin Callahan shares what startup fundraising actually required at Hopscotch: $7.5 million across pre-seed and seed, conversations with 150 to 200 VCs per round, and roughly 1,000 hours of work. He and Hunter also discuss leaving big tech, fundraising through the 2023 downturn, the financial and personal strain of startup life, and Kevin's case for targeted investor outreach over mass automated messages. Founders preparing to raise will get a realistic account of the work behind the funding announcement. Chapters 00:00 Fundraising persistence 00:33 Introducing Kevin Callahan and Hopscotch 01:41 What working at Twitter was really like 03:55 Global platform responsibility and China 09:12 Why Twitter became culturally influential 13:04 Leaving big tech to start a company 16:22 Fundraising during the 2023 downturn 19:26 The personal cost of startup life 21:07 Fundraising outcomes and founder reality 25:43 Cold outreach and investor introductions 30:50 Hopscotch and closing Host: R. Hunter Harris https://www.linkedin.com/in/rhunterharris/ Guest: Kevin Callahan https://www.linkedin.com/in/kevgcallahan/ https://hopscotchlabs.ai/ By Hunter Software Consulting https://huntersoftwareconsulting.com/

  4. Sep 13

    Hunter Harris: Product Sprawl - Why Every New Platform Multiplies the Cost

    In this episode, R. Hunter Harris explains how product decisions ripple through an organization, why building and maintaining multiple product surfaces multiplies development and QA work, and how platform-specific demands can fracture a supposedly narrow ICP. He shows why better AI and process improvements cannot erase the underlying scaling math, then makes the business case for serving one target segment completely before expanding. Perfect for B2B SaaS founders deciding which platforms, product promises, and customer needs to prioritize for profitable growth. Chapters 00:00 The cost of sales you cannot support 01:06 Challenges of building multiple product surfaces 05:38 How product divergence multiplies development and QA work 09:39 Narrowing down to one ICP before expanding Host: R. Hunter Harris https://www.linkedin.com/in/rhunterharris/ By Hunter Software Consulting https://huntersoftwareconsulting.com/

  5. Sep 6

    Hunter Harris: Business vs. Hobby - Why Side Hustles Need Customers

    In this solo episode, Hunter Harris digs into the difference between a hobby and a business. Hobbies are internally directed. Businesses answer to customers. If you're building a side hustle without customer conversations, customer discovery, and working unit economics, you may have a project - but you don't have much of a business. Hunter explains why successful businesses often become boring, why your time is usually the most expensive input, how multiple side hustles dilute focus, and why monetizing a hobby can kill the joy that made it worthwhile. He closes with Ship to Learn: a way to preserve experimentation while staying focused on customers and building something people will actually pay for. Chapters 00:00 Why side hustles fail without customers 00:23 Build and Break Through intro 00:30 Business or hobby? 00:57 External direction vs. self-direction 01:06 Why successful businesses become boring 04:35 What hobbies are actually for 05:59 The messy middle: monetized hobbies 06:24 Unit economics and the true cost of your time 09:06 A business requires customer conversations 09:33 Why multiple side hustles dilute focus 10:54 When monetizing a hobby kills the joy 12:05 Customers may not want what you built 12:33 The danger of becoming a market of one 14:15 Ship to Learn: exploration with customer focus 15:35 The through line: focus on the customer 16:27 Closing Host: R. Hunter Harris https://www.linkedin.com/in/rhunterharris/ By Hunter Software Consulting https://huntersoftwareconsulting.com/

  6. Aug 30

    Aly Madhavji: Fundraising Readiness for Founders

    In this episode, Aly Madhavji shares expert insights on fundraising readiness, pitch deck optimization, and building strong investor relationships. Perfect for founders looking to accelerate their fundraising success and improve their pitch strategies. Chapters 00:00 Introduction to Aly Madhavji and his background 02:42 Fundraising readiness: How founders should prepare 03:02 Common challenges in fundraising and how to overcome them 04:52 The 90-step process for startup fundraising preparation 05:21 Using AI to analyze pitch decks and improve fundraising 06:17 Best practices for pitch decks and investor outreach 07:13 The importance of a strong 11, 30, and 90-second pitch 08:37 How to craft compelling key sentences for pitches 09:12 Examples of effective pitch hooks and pitches 11:10 Reinforcing your pitch and maintaining clarity 12:50 Common pitfalls in boardroom pitches and subtle errors 16:52 Ingredients of a successful pitch and presentation 17:36 Tracking progress and demonstrating momentum 19:08 The value of regular updates and transparency 20:27 Choosing the right investors and managing relationships 22:46 The importance of velocity and foundation for scaling 24:32 Building a strong foundation before scaling 27:26 Identifying helpful versus problematic investors 30:23 Aly Madhavji's resources and contact information 31:23 Closing remarks and key takeaways from the episode Host: R. Hunter Harris https://www.linkedin.com/in/rhunterharris/ Guest: Aly Madhavji https://www.linkedin.com/in/alymadhavji/ https://blockchainff.com/ https://www.amazon.com/dp/B0F4FKVWRH?lv=shuf&channelId=500&plpRedirect=mhFallback (Pitch Deck Tool to follow) By Hunter Software Consulting https://huntersoftwareconsulting.com/

  7. Aug 23

    Jeff Goldblatt: Startups, Entrepreneurship, and Risk

    In this episode, Jeff Goldblatt shares insights on startup success and failure, survivorship bias, and the importance of realistic expectations for founders. He discusses how founders can better understand the true odds of success and the value of learning through small experiments. Host: R. Hunter Harris https://www.linkedin.com/in/rhunterharris/ Guest: Jeff Goldblatt https://www.linkedin.com/in/iamnotaceo/ https://thewhatevernetwork.com/collections/cofounderator By Hunter Software Consulting https://huntersoftwareconsulting.com/

  8. Aug 16

    Joel Tosi: High Functioning Product Engineering Teams

    In this episode, Hunter Harris interviews Joel Tosi about high-functioning product teams, integration, customer feedback, and the importance of focusing on strategy over reaction. They explore how organizations can improve their product delivery and organizational culture. Chapters 00:00 Introduction of Joel Tosi and episode overview 00:33 Hunter introduces the topic of high-functioning product teams 01:39 The importance of customer observation and feedback 02:09 Real-world example of customer feedback improving product 02:36 High-functioning teams and intuitive problem solving 02:46 The role of integration and silos in organizations 03:16 Problems caused by organizational silos and lack of customer access 04:04 Using tools to trace user journeys and bugs 04:38 The importance of talking directly to users 06:21 Limitations of tools and the need for direct customer interaction 07:14 Customer experience during internet outages and upselling 08:08 Device diversity and the challenge of multi-platform support 09:21 Organizational culture and the separation of strategy and execution 10:13 The recurring lesson of strategy and execution over time 11:04 The impact of AI on speed and strategy 11:37 Opportunity cost of fast execution and wrong strategy 12:16 Market risks and the cost of building the wrong product 13:02 Feedback loops and learning from user data 13:35 The importance of evaluating success and ROI 14:20 Product surface area growth and organizational capacity 14:50 The complexity of multiple features and A/B testing 15:21 The pitfalls of process theater and fake metrics 16:09 Rebranding and superficial changes versus real product improvements 17:02 Technical debt versus product debt and feature flags 17:37 Managing feature flags and avoiding nested permutations 18:29 The risks of large batches and delayed feedback 19:20 The danger of building the wrong thing and sunk cost fallacy 20:29 Focusing on high-value customers and product prioritization 21:19 Customer-centric versus product-centric mindset 22:05 Being obsessed with customer needs and opinionation 23:01 The importance of clear product vision and niching 23:25 Avoiding cowardly sales tactics and over-customization 24:15 Opportunity cost of maintaining unnecessary features 25:01 Economic thinking and opportunity cost in product decisions 26:11 Small bets and iterative development 28:17 Embracing uncertainty and learning through small experiments 29:02 The value of continuous deployment and quick rollback 30:16 Risks of large changes and building the wrong thing 30:45 The cascade of technical and product debt 31:17 Upcoming book release and call for critical thinking 32:13 The importance of fun and joy in software engineering Host: R. Hunter Harris https://www.linkedin.com/in/rhunterharris/ Guest: Joel Tosi https://www.linkedin.com/in/joel-tosi-531a3b/ https://www.simonandschuster.com/books/Signals-Levers/Elisabeth-Hendrickson/9781966280293 https://www.dojoandco.com/ By Hunter Software Consulting https://huntersoftwareconsulting.com/

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Ratings & Reviews

5
out of 5
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About

Most startups don't die from bad ideas. They die from the same handful of mistakes, made over and over, that nobody warned them about. Build and Break Through is Hunter Harris - fractional CPTO, advisor, and four-exit operator - in real conversations with the founders, builders, and operators who've lived it and are living it. The wins, the wrecks, and the hard-won lessons in between. Hunter's spent years watching the same questions sink good companies. This show takes the answers out of the boardroom and into yours - give-first, no fluff - so founders can ship, survive, scale, and succeed.

Information

  • Creator
    R. Hunter Harris
  • Years Active
    2026
  • Episodes
    35
  • Rating
    Clean
  • Copyright
    © 2026 R. Hunter Harris
  • Show Website
    Build & Break Through