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

    Danny Davis: Cheaper to Start, Not Cheaper to Build

    Danny Davis took a company public, sold another, and is now building StackYak. "AI is making things more efficient, but it's still expensive to build a company." Founders say "we only need 500,000." What if you need two million? "You fail before you finish." We also get into why the company's lawyer is not your lawyer, why you take the small check that gets you to the next round, and why "debt is still cheaper than equity." Chapters 00:00 People are craving real relationships 00:21 Meet Danny Davis 01:08 Why start a third company? 05:22 AI isn't making things cheaper yet 07:18 The truth about taking a company public 08:59 Selling for less and planning for taxes 11:19 The second exit: Origin Labs 14:24 The company's lawyer is not your lawyer 16:01 Why founders skip legal help 17:20 Don't let ChatGPT write your contracts 19:44 Where AI helps with legal documents 20:25 What he'd do differently: due diligence 21:54 The right investors are your friend 24:21 Investors who do more than write a check 25:54 Get into an accelerator early 27:08 Co-founders versus solo founders 28:20 Take the small check 29:10 Cheaper to start, not cheaper to build 30:30 Debt, grants and specialty investors 32:49 What StackYak is building 33:34 Real conversations, real discovery Host: R. Hunter Harris https://www.linkedin.com/in/rhunterharris/ Guest: Danny Davis https://www.linkedin.com/in/dannydavis12/ https://stackyak.ai/ Newsletter: Don't SaaS Me https://hunter-software-consulting.beehiiv.com/ By Hunter Software Consulting https://huntersoftwareconsulting.com/

  2. Oct 18

    Jeff Patton: Build What Customers Will Use

    A company Jeff Patton worked with this year shipped a glossy new release to 2.65 million customers. AI helped them get it out on time. It didn't break. There were no bugs. Nobody liked it. Jeff, author of User Story Mapping, joins me to talk about dual track development. He says the book needs a second edition: it described a discovery team and a delivery team, but after 10 years of coaching he sees two tracks and one team, with engineers and testers pulled up into discovery. Jeff asks the whole team, on a scale of 1 to 5, how confident they are that people will see a feature and want to try it. If one says 3 and another says 5, ask what they'd need to learn to be sure. Keep using is the hard one to test: release something usable to a small group, and in Jeff's words, "don't build it at scale." We also get into release to learn versus release to earn, and what I've seen in client GitHub repos since they adopted AI: a lot more output, but the share of work going toward customer results is flat or down. Jeff on asking AI what customers think: "the AI is not your customer." His homework: do an opportunity canvas for the feature you're working on right now. If you can't say who it's for, what problem it solves and how you'll measure it, stop building it. Chapters 00:00 A release customers did not like 00:21 Meet Jeff Patton 04:54 Discovery and delivery together 07:33 Two tracks within one team 09:46 Expose the beliefs behind a feature 12:52 Where does the team's confidence differ? 13:58 A usable release that teaches you something 16:03 Learning about technical risk 17:16 Ship to learn, earn, or burn 23:24 AI output and customer outcomes 27:40 AI opinion and actual customer evidence 33:18 An exercise for the next feature 34:46 Where to learn more from Jeff Host: R. Hunter Harris https://www.linkedin.com/in/rhunterharris/ Guest: Jeff Patton https://www.linkedin.com/in/productdesigncoach https://jpattonassociates.com/ Newsletter: Don't SaaS Me https://hunter-software-consulting.beehiiv.com/ By Hunter Software Consulting https://huntersoftwareconsulting.com/

  3. Oct 11

    Making AI Useful with David Rasch

    How much of the feedback on a release actually needs to block it? David Rasch looks for the checks his team can automate so nobody has to keep thinking about them. If an agent repeatedly makes the same mistake, a deterministic check can catch it before a person spends another review pointing it out. That leaves the person reviewing the work to decide what matters. We talk about where to spend that judgment: the data model, changes to the interface, and the parts of a system that need careful design. Code may be easier to replace now, but someone still has to understand what the software is supposed to do. David gives an example of an AI review getting caught up in a race condition for a task that runs about once a month. In that case, he decided the extra complexity wasn't worth it. I share an experiment where repeatedly responding to review feedback left my project unable to do anything at all. The useful question is what needs fixing before this release, and what can become a separate ticket whose priority you decide later. A patient reviewer can always find more work. You still need a person who can decide when the work is worth doing. Useful questions from the conversation Which repeated review comments could become automatic checks? Which parts of this change need someone to understand the design? Does this issue need to stop the release, or can you decide its priority separately? Chapters 00:00 When AI agrees with everything 00:12 Meet David Rasch 02:12 What you still need to understand 05:02 Data foundations before more code 10:00 Building and selling as an engineering education 14:42 Which parts need careful design? 19:12 Automating repeatable review checks 21:20 Code is easier to rework 22:31 When review becomes a loop 25:02 Human judgment and work worth doing 28:55 Where to find David Host: R. Hunter Harris https://www.linkedin.com/in/rhunterharris/ Guest: David Rasch https://www.linkedin.com/in/rasch Newsletter: Don't SaaS Me https://hunter-software-consulting.beehiiv.com/ By Hunter Software Consulting https://huntersoftwareconsulting.com/

  4. Oct 4

    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 Host: R. Hunter Harris https://www.linkedin.com/in/rhunterharris/ Guest: Josh Colter https://www.linkedin.com/in/joshcolter https://cardboardit.com/ Newsletter: Don't SaaS Me https://hunter-software-consulting.beehiiv.com/ By Hunter Software Consulting https://huntersoftwareconsulting.com/

  5. 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/ Newsletter: Don't SaaS Me https://hunter-software-consulting.beehiiv.com/ By Hunter Software Consulting https://huntersoftwareconsulting.com/

  6. 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/ Newsletter: Don't SaaS Me https://hunter-software-consulting.beehiiv.com/ By Hunter Software Consulting https://huntersoftwareconsulting.com/

  7. 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/ Newsletter: Don't SaaS Me https://hunter-software-consulting.beehiiv.com/ By Hunter Software Consulting https://huntersoftwareconsulting.com/

  8. 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/ Newsletter: Don't SaaS Me https://hunter-software-consulting.beehiiv.com/ By Hunter Software Consulting https://huntersoftwareconsulting.com/

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Ratings & Reviews

5
out of 5
2 Ratings

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
    38
  • Rating
    Clean
  • Copyright
    © 2026 R. Hunter Harris
  • Show Website
    Build & Break Through