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May 23, 2018 · 23m · top-founders

1033 Couple Cashes Out 401k in 2010, Now Doing $15m/Year

Nathan Latka · 9m spoken Brian Miles · 6m spoken Shannon Miles · 4m spoken
0:00 / 0:00

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In this episode of The Top Entrepreneurs, Nathan Latka interviews Belay co-founders Brian and Shannon Miles on how they bootstrapped a remote virtual assistant and bookkeeping firm from 401(k) savings to nearly $15 million in annual revenue. They discuss their high-touch relationship management model, selective contractor hiring, unit economics, and future expansion into proprietary technology.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 45.8% of the talking time here. How this is scored →

Nathan as informed peer 5.6 Guest teaching 2.7 Guest disagreement 1.0 Nathan pushing back 2.4
05100:0010:0020:000:49–4:36 · Nathan as informed peer 5/10 Meeting Brian and Shannon Miles and Belay's Origins Nathan frames the basic agency unit economics simply as markups on talent, which the founders validate while clarifying their high-touch relationship manager differentiator. The tone is collaborative and informative with zero friction.4:36–7:12 · Nathan as informed peer 6/10 Bootstrapping, Ownership Structure, and Unit Economics Nathan calculates margin expectations and COGS lines for services businesses, digging into the 51/49 female-owned equity split and breakeven timeline. The founders readily share figures and confirm their targeted 50% gross margin.7:13–9:41 · Nathan as informed peer 6/10 Scaling Revenue, Hiring Rigor, and Managing Competition Nathan sets up an aggressive competitor roleplay where Zirtual raises $100M to poach talent. Brian counters by explaining Zirtual's past financial implosion and their own low-churn client qualification strategy.9:43–14:10 · Nathan as informed peer 5/10 Sponsor Break: ProsperWorks CRM Integration and Benefits Following a sponsor read, Nathan challenges the marketplace moat using an Uber/Lyft multi-apping comparison. Shannon explains how their high-touch model and capacity-matching retain contractor loyalty.14:11–17:20 · Nathan as informed peer 6/10 Contractor Retention and Relationship Management Processes Nathan shares his personal frustration as a client dealing with contractor churn. Brian and Shannon school him on how their low-margin relationship management layer proactively handles seamless handoffs and training.17:21–20:34 · Nathan as informed peer 7/10 Exit Considerations and Expanding into Proprietary Software Nathan crunches their bottom line math and cites industry examples like Hootsuite and Infusionsoft to argue for building proprietary tech. Shannon notes they are running Google Sprints to explore tech solutions.20:34–22:56 · Nathan as informed peer 4/10 The Famous Five Questions and Episode Conclusion Nathan runs through the standard Famous Five rapid-fire questions, focusing on Shannon as majority owner, followed by a recap of Belay's key metrics.0:49–4:36 · Guest teaching 3/10 Meeting Brian and Shannon Miles and Belay's Origins Nathan frames the basic agency unit economics simply as markups on talent, which the founders validate while clarifying their high-touch relationship manager differentiator. The tone is collaborative and informative with zero friction.4:36–7:12 · Guest teaching 2/10 Bootstrapping, Ownership Structure, and Unit Economics Nathan calculates margin expectations and COGS lines for services businesses, digging into the 51/49 female-owned equity split and breakeven timeline. The founders readily share figures and confirm their targeted 50% gross margin.7:13–9:41 · Guest teaching 3/10 Scaling Revenue, Hiring Rigor, and Managing Competition Nathan sets up an aggressive competitor roleplay where Zirtual raises $100M to poach talent. Brian counters by explaining Zirtual's past financial implosion and their own low-churn client qualification strategy.9:43–14:10 · Guest teaching 3/10 Sponsor Break: ProsperWorks CRM Integration and Benefits Following a sponsor read, Nathan challenges the marketplace moat using an Uber/Lyft multi-apping comparison. Shannon explains how their high-touch model and capacity-matching retain contractor loyalty.14:11–17:20 · Guest teaching 4/10 Contractor Retention and Relationship Management Processes Nathan shares his personal frustration as a client dealing with contractor churn. Brian and Shannon school him on how their low-margin relationship management layer proactively handles seamless handoffs and training.17:21–20:34 · Guest teaching 3/10 Exit Considerations and Expanding into Proprietary Software Nathan crunches their bottom line math and cites industry examples like Hootsuite and Infusionsoft to argue for building proprietary tech. Shannon notes they are running Google Sprints to explore tech solutions.20:34–22:56 · Guest teaching 1/10 The Famous Five Questions and Episode Conclusion Nathan runs through the standard Famous Five rapid-fire questions, focusing on Shannon as majority owner, followed by a recap of Belay's key metrics.0:49–4:36 · Guest disagreement 1/10 Meeting Brian and Shannon Miles and Belay's Origins Nathan frames the basic agency unit economics simply as markups on talent, which the founders validate while clarifying their high-touch relationship manager differentiator. The tone is collaborative and informative with zero friction.4:36–7:12 · Guest disagreement 1/10 Bootstrapping, Ownership Structure, and Unit Economics Nathan calculates margin expectations and COGS lines for services businesses, digging into the 51/49 female-owned equity split and breakeven timeline. The founders readily share figures and confirm their targeted 50% gross margin.7:13–9:41 · Guest disagreement 2/10 Scaling Revenue, Hiring Rigor, and Managing Competition Nathan sets up an aggressive competitor roleplay where Zirtual raises $100M to poach talent. Brian counters by explaining Zirtual's past financial implosion and their own low-churn client qualification strategy.9:43–14:10 · Guest disagreement 1/10 Sponsor Break: ProsperWorks CRM Integration and Benefits Following a sponsor read, Nathan challenges the marketplace moat using an Uber/Lyft multi-apping comparison. Shannon explains how their high-touch model and capacity-matching retain contractor loyalty.14:11–17:20 · Guest disagreement 1/10 Contractor Retention and Relationship Management Processes Nathan shares his personal frustration as a client dealing with contractor churn. Brian and Shannon school him on how their low-margin relationship management layer proactively handles seamless handoffs and training.17:21–20:34 · Guest disagreement 1/10 Exit Considerations and Expanding into Proprietary Software Nathan crunches their bottom line math and cites industry examples like Hootsuite and Infusionsoft to argue for building proprietary tech. Shannon notes they are running Google Sprints to explore tech solutions.20:34–22:56 · Guest disagreement 0/10 The Famous Five Questions and Episode Conclusion Nathan runs through the standard Famous Five rapid-fire questions, focusing on Shannon as majority owner, followed by a recap of Belay's key metrics.0:49–4:36 · Nathan pushing back 2/10 Meeting Brian and Shannon Miles and Belay's Origins Nathan frames the basic agency unit economics simply as markups on talent, which the founders validate while clarifying their high-touch relationship manager differentiator. The tone is collaborative and informative with zero friction.4:36–7:12 · Nathan pushing back 2/10 Bootstrapping, Ownership Structure, and Unit Economics Nathan calculates margin expectations and COGS lines for services businesses, digging into the 51/49 female-owned equity split and breakeven timeline. The founders readily share figures and confirm their targeted 50% gross margin.7:13–9:41 · Nathan pushing back 4/10 Scaling Revenue, Hiring Rigor, and Managing Competition Nathan sets up an aggressive competitor roleplay where Zirtual raises $100M to poach talent. Brian counters by explaining Zirtual's past financial implosion and their own low-churn client qualification strategy.9:43–14:10 · Nathan pushing back 3/10 Sponsor Break: ProsperWorks CRM Integration and Benefits Following a sponsor read, Nathan challenges the marketplace moat using an Uber/Lyft multi-apping comparison. Shannon explains how their high-touch model and capacity-matching retain contractor loyalty.14:11–17:20 · Nathan pushing back 2/10 Contractor Retention and Relationship Management Processes Nathan shares his personal frustration as a client dealing with contractor churn. Brian and Shannon school him on how their low-margin relationship management layer proactively handles seamless handoffs and training.17:21–20:34 · Nathan pushing back 3/10 Exit Considerations and Expanding into Proprietary Software Nathan crunches their bottom line math and cites industry examples like Hootsuite and Infusionsoft to argue for building proprietary tech. Shannon notes they are running Google Sprints to explore tech solutions.20:34–22:56 · Nathan pushing back 1/10 The Famous Five Questions and Episode Conclusion Nathan runs through the standard Famous Five rapid-fire questions, focusing on Shannon as majority owner, followed by a recap of Belay's key metrics.

speaking balance: gold is Nathan, purple is the guest (3 minute bins)

0:00 · Nathan 59% · guest 41%0:00 · Nathan 59% · guest 41%3:00 · Nathan 30.3% · guest 69.7%3:00 · Nathan 30.3% · guest 69.7%6:00 · Nathan 41.3% · guest 58.7%6:00 · Nathan 41.3% · guest 58.7%9:00 · Nathan 63.1% · guest 36.9%9:00 · Nathan 63.1% · guest 36.9%12:00 · Nathan 44.3% · guest 55.7%12:00 · Nathan 44.3% · guest 55.7%15:00 · Nathan 37.3% · guest 62.7%15:00 · Nathan 37.3% · guest 62.7%18:00 · Nathan 30.4% · guest 69.6%18:00 · Nathan 30.4% · guest 69.6%21:00 · Nathan 69.5% · guest 30.5%21:00 · Nathan 69.5% · guest 30.5%
Sharpest disagreement ▶ 9:06 Brian dismisses Zirtual threat by highlighting their implosion

Brian directly counters Nathan's hypothetical competitor attack by pointing out that Zirtual previously mismanaged money and collapsed under growth pressure.

 Hardest push from Nathan ▶ 8:30 Nathan roleplays aggressive well-funded competitor poaching

Nathan aggressively tests their defenses by acting as a venture-backed competitor raising $100M specifically to outbid their contractor wages.

 Biggest teaching moment ▶ 16:11 Shannon explains how Belay preemptively replaces sub-par matches

Shannon educates Nathan on their proactive account management strategy, explaining they actively replace contractors before clients even complain about mediocre service.

 Nathan holds their own ▶ 18:56 Nathan details case studies of agencies successfully pivoting to SaaS

Nathan showcases domain expertise by citing historical revenue and growth trajectories of Hootsuite and Infusionsoft pivoting from agency roots to multi-million SaaS businesses.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Meeting Brian and Shannon Miles and Belay's Origins 5312 Nathan frames the basic agency unit economics simply as markups on talent, which the founders validate while clarifying their high-touch relationship manager differentiator. The tone is collaborative and informative with zero friction.
Bootstrapping, Ownership Structure, and Unit Economics 6212 Nathan calculates margin expectations and COGS lines for services businesses, digging into the 51/49 female-owned equity split and breakeven timeline. The founders readily share figures and confirm their targeted 50% gross margin.
Scaling Revenue, Hiring Rigor, and Managing Competition 6324 Nathan sets up an aggressive competitor roleplay where Zirtual raises $100M to poach talent. Brian counters by explaining Zirtual's past financial implosion and their own low-churn client qualification strategy.
Sponsor Break: ProsperWorks CRM Integration and Benefits 5313 Following a sponsor read, Nathan challenges the marketplace moat using an Uber/Lyft multi-apping comparison. Shannon explains how their high-touch model and capacity-matching retain contractor loyalty.
Contractor Retention and Relationship Management Processes 6412 Nathan shares his personal frustration as a client dealing with contractor churn. Brian and Shannon school him on how their low-margin relationship management layer proactively handles seamless handoffs and training.
Exit Considerations and Expanding into Proprietary Software 7313 Nathan crunches their bottom line math and cites industry examples like Hootsuite and Infusionsoft to argue for building proprietary tech. Shannon notes they are running Google Sprints to explore tech solutions.
The Famous Five Questions and Episode Conclusion 4101 Nathan runs through the standard Famous Five rapid-fire questions, focusing on Shannon as majority owner, followed by a recap of Belay's key metrics.

Statements from this episode (9)

Disclosure
Shannon Miles: Belay was funded in 2010 by cashing out a 401(k)
“We spent our twenties getting in a lot of debt. And getting out of it and actually saving and having a four Oh one K that we used in 2010 to fund our businesses.”
Shannon Miles May 23, 2018 ▶ 2:03
Assertion Not checkable as stated
Brian Miles: Worldwide 101 is Belay's closest direct competitor
“I would say our closest competitor is worldwide. One-on-one they're based over in London. But they do operate here in the States.”
Brian Miles May 23, 2018 ▶ 4:15
Assertion Not checkable as stated
Brian Miles: Bootstrapped Belay reached profitability in 14 months
“We have not raised a dime in capital for our business. We bootstrapped it all. We've got the profitability around 14 months in.”
Brian Miles May 23, 2018 ▶ 4:38
Assertion Not checkable as stated
Brian Miles: Belay equity is split 51/49 in Shannon's favor
“Well, it's a 51, 49. It's not that far off, but it's majority owned by a woman.”
Brian Miles May 23, 2018 ▶ 4:54
Assertion Not checkable as stated
Brian Miles: Belay finished 2017 with nearly $15 million in revenue
“We ended the year just shy of 15.”
Brian Miles May 23, 2018 ▶ 7:21
Assertion Not checkable as stated
Shannon Miles: Belay employs 61 staff and roughly 500 contractors
“Yeah, we have about 500 contractors with our team right now, and about 61 employees here in the Atlanta metro area.”
Shannon Miles May 23, 2018 ▶ 7:36
Assertion Not checkable as stated
Shannon Miles: Belay accepts only 2% of contractor applicants
“Now, we only bring on about two percent of the resumes that we get, so we're Very selective in who we partner with because it has to check a lot of boxes.”
Shannon Miles May 23, 2018 ▶ 7:52
Assertion Supported
Brian Miles: Zirtual imploded due to poor financial management
“Zurchal imploded two years ago and was sold to this organization that now owns it in Columbus, Ohio, because they didn't manage their money very well.”
Brian Miles May 23, 2018 ▶ 9:16
Assertion Supported
Latka: Infusionsoft generates around $120M in ARR
“He started as a consultancy in 2002, now doing about one hundred and twenty million in ARR.”
Nathan Latka May 23, 2018 ▶ 20:22
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