Dec 3, 2020 · 1h 3m · we-live-to-build
The Secret Weapon That Quietly Beats Every Competitor
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of the 'We Live to Build' podcast, host Sean Weisbrot and 10 Mile Square Managing Director Frank Olschlager examine how enterprise automation, modern SaaS architectures, and disciplined engineering practices drive sustainable business growth and operational efficiency.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Sean holds 32.6% of the talking time here. How this is scored →
Sean as informed peer 4.1 Guest teaching 4.1 Guest disagreement 0.5 Sean pushing back 0.9
speaking balance: gold is Sean, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 49:30 Frank Explicitly Reframing the Host's Question
Frank openly redirects the conversation by stating he is changing Sean's prompt because a different topic is more valuable to discuss.
Hardest push from Sean ▶ 18:09 Sean Correcting Frank on Salesforce Acquiring SlackSean steps in immediately to correct Frank's assumption that Microsoft was buying Slack, confirming Salesforce's $27.7 billion acquisition.
Biggest teaching moment ▶ 28:35 Architecting Searchable Digital Archives via CaptionsFrank educates the host on how his team designed an automated ingestion pipeline indexing time-coded closed captions to make decades of legacy video searchable.
Sean holds their own ▶ 19:42 Sean Breaking Down Slack's Financials and 60x ValuationSean demonstrates deep market analysis by calculating Slack's $200M yearly burn rate and challenging its 60x revenue multiple valuation.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Sean as informed peer | Guest teaching | Guest disagreement | Sean pushing back | Why |
|---|---|---|---|---|---|---|
| Frank Olschlager's Entrepreneurial Origins and Career Journey | 3 | 2 | 1 | 2 | Frank politely clarifies that he was not an original founder of 10 Mile Square. Sean lightly defends his intro, noting he had only introduced Frank as managing director. | |
| The Imperative of Digital Transformation and Cloud Automation | 4 | 3 | 0 | 0 | Frank outlines the competitive necessity of cloud automation. Sean interjects with his own startup's experience implementing automated mobile build pipelines early on. | |
| Defining Automation and Its Future with Machine Learning | 2 | 5 | 0 | 0 | Frank provides a clear conceptual definition of automation as repeatable execution and projects how machine learning algorithms will integrate into automation chains. | |
| Entry-Level Automation: Autoresponders and Integrated CRM Workflows | 3 | 4 | 1 | 1 | Frank highlights autoresponders and CRM routing as baseline automation. When Sean asks if companies should build custom autoresponders, Frank firmly advises against reinventing commoditized tech. | |
| Selecting Specialized Automation Toolsets Across Operations | 2 | 4 | 1 | 0 | Frank candidly remarks that he dislikes all automation tools as necessary evils and delineates the difference between marketing front-end tools and technical infrastructure tools like Terraform and Jenkins. | |
| Analyzing Salesforce's Acquisition of Slack and SaaS Multiples | 8 | 2 | 1 | 5 | Sean corrects Frank when Frank mistakes the Slack buyer for Microsoft. Sean demonstrates strong domain expertise by calculating Slack's 60x revenue multiple and financial burn rate. | |
| Intermediate Automation: CI/CD Pipelines and Founder Upskilling | 7 | 4 | 0 | 0 | Frank defines CI/CD pipelines. Sean demonstrates impressive technical familiarity by explaining his team's Git flow, feature branch regression testing, and manual staging promotions. | |
| Case Study: Architecting Digital Automation for Legacy Media | 1 | 6 | 0 | 0 | Frank delivers an in-depth case study of transforming a physical tape-based media company into a digital asset management system using indexed time-coded closed captioning. | |
| Engineering Pitfalls: Lost Source Code and Rogue Developers | 6 | 5 | 0 | 1 | Frank recounts discovering a client was running production systems without source code. Sean matches the story with his own experience managing a rogue backend developer who ignored architectural wiki documentation. | |
| Business Alignment, Scalability, and the Architectural Shift to SaaS | 3 | 6 | 0 | 0 | Frank breaks down the technical and business evolution from non-scalable Application Service Providers (ASPs) to modern multi-tenant SaaS architectures with shared infrastructure. | |
| Comparing Venture Capital and Bootstrapped Growth Strategies | 6 | 4 | 1 | 2 | Both host and guest exchange sharp business insights on venture capital dynamics versus organic growth, comparing founder equity dilution with bootstrap profitability. | |
| Goal Setting and Aligning Ambitions with Core Values | 2 | 5 | 2 | 1 | Frank explicitly reframes Sean's question to share a foundational leadership lesson on writing down goals and auditing them against core personal values like family. | |
| Workplace Evolution: Company Culture, Values, and Generational Shifts | 6 | 3 | 0 | 0 | Sean leads an analysis of generational shifts in workplace culture citing Coinbase and Gen Z expectations. Frank validates this with a story about his father's rigid legacy corporate dress code. |
Statements from this episode (13)
Olschlager: Companies lacking cloud automation cannot compete in modern markets
“If you're not automated in how you operate in the cloud, you're not even going to be able to compete in today's market.”
Olschlager: Integrating Machine Learning into Automation Is Already in Production
“When you look at the convergence of multiple technologies you know, say machine learning type algorithms, and, you know, you start to hook those into your automation chain you know, then you can start to think of some really interesting ways to do things that,…”
Olschlager: Never build custom autoresponders unless competing in marketing automation
“Really, I can think of no circumstance that I would tell a team to build their own autoresponder, unless we were going to take on the,
Marketing automation market, and we had to have that native functionality. You know, if I'm just a company selling widgets, …”
Weisbrot: Slack Is Losing Almost $200 Million a Year
“And they're basically losing like almost two hundred million dollars a year right now.”
Weisbrot: Slack's 60x revenue multiple sale to Salesforce is insane
“So my back of the paper calculation was that they just sold for 60 times a multiple of their revenue. Which is insane for SAS.”
Olschlager: Amazon and Spotify deploy hundreds of daily changes in under an hour
“When you think about companies like Spotify or Amazon
you know, other, other sort of big, you know, high tech companies like that, you know, they push out, you know, hundreds, if not thousands of change, changes into production every day. And, you know, they'…”
Weisbrot: Founders must technically upskill to oversee what their engineering teams build
“Part of learning how to automate your company is also upskilling yourself as a founder so that you can understand what the hell is going on in your company. Especially on the tech side, because so many, I I've heard of so many people building something and lik…”
Olschlager: SaaS Enables Revenue Scalability That ASP Models Failed to Deliver
“SAS as a technology sustainably enables a growth revenue capability that application service provider did not.”
Olschlager: Raising $10M in VC requires a $100M exit to get rich
“You take ten million dollars from a VC, you know, you better be talking about, you know, a hundred million dollars at a minimum, you know, if you think you're going to get rich off the deal.”
Weisbrot: Butterfield will leave Slack within two years of Salesforce acquisition
“I imagine he may spend the next two years just staying on a CEO working on who's going to replace him so he can become chairman. Chances are that'll be someone from Salesforce walking in for like maybe some VP somewhere will end up running Slack in two or thre…”
Olschlager: Public company CEOs spend very little time with their families
“When you're the CEO of a public company, you don't Actually spend a lot of time at home at the dinner table or with your kids.”
Weisbrot: 14% of Coinbase staff resigned over Brian Armstrong's non-political mandate
“And I think his name is Brian Armstrong, the CEO of Coinbase, said basically, we are a non-political organization. If you don't like that, you can quit. And I think five, 14% of the company quit”
Olschlager: Leaders Ignoring Employee Social Needs Will Lose Their Workforce
“And a company now really acts much more like a, an organic social organism. And if leadership Isn't responding to, you know, the needs of that organism. They're going to find themselves without a viable workforce, you know, pretty quickly.”