Build & Break Through

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

Find David: https://www.linkedin.com/in/rasch

Listen to Episode 36 of Build & Break Through: https://buildandbreakthrough.riverside.com/e/making-ai-useful-with-david-rasch

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

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/

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/

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/

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/

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
https://investment.blockchainff.com/satoshi/

By Hunter Software Consulting
https://huntersoftwareconsulting.com/

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/

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/

In this episode, Alan Page shares his insights on high-performing engineering teams, focusing on transparency, accountability, and psychological safety. Discover practical strategies to foster a culture of trust, effective communication, and continuous improvement.

Chapters

00:00 Introduction and guest background

02:15 The importance of transparency in leadership

04:10 Modeling behavior and encouraging feedback

05:02 The origin of the triangle framework

05:50 Insights from leadership books and models

07:40 Pink’s Drive and the connection to team culture

09:22 Turning principles into actionable behaviors

10:20 Success stories and real-world examples

11:02 The role of transparency in team trust

12:01 Practicing transparency through regular meetings

13:04 Handling sensitive questions and building safety

14:43 The importance of leaders admitting mistakes

15:17 The value of regular one-on-ones and skip-levels

16:37 Involving team in hiring decisions

18:14 The significance of caring about team members

20:21 Navigating accountability extremes

21:17 Estimation and planning with probabilistic methods

23:38 Learning from missed deadlines and continuous improvement

26:02 Using red, yellow, green signals for project status

27:03 Closing remarks and resources

Host: R. Hunter Harris
https://www.linkedin.com/in/rhunterharris/

Guest: Alan Page
https://www.linkedin.com/in/a-l-a-n/
https://angryweasel.substack.com/
https://podcasts.apple.com/us/podcast/ab-testing/id856528068

By Hunter Software Consulting
https://huntersoftwareconsulting.com/