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Mar 20, 2020 · 19m · top-founders

1700 How A Bootstrapped $3m Revenue CEO Plans to Handle Virus, Potential Cashflow Issues

Steve Benson · 11m spoken Nathan Latka · 6m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

Badger Maps CEO Steve Benson joins Nathan Latka to discuss navigating pandemic-induced market disruptions through customer retention discounts, healthcare routing pivots, and non-dilutive venture debt financing.

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 34.6% of the talking time here. How this is scored →

Nathan as informed peer 5.0 Guest teaching 3.0 Guest disagreement 0.2 Nathan pushing back 0.8
05100:0010:000:56–3:51 · Nathan as informed peer 4/10 Pandemic Impact and Exploring Healthcare Pivots Nathan frames the macro problem facing field sales during early COVID-19 lockdowns. Steve collaboratively explains the business impact and details how Badger Maps is exploring pivots into home-visit healthcare logistics.3:51–8:28 · Nathan as informed peer 5/10 Customer Retention Tactics and Discounting Strategies Nathan asks about metrics and cancellation strategies during lockdown. Steve explains his policy of offering individual churn-risk users half off for three months while maintaining standard terms for enterprise accounts.8:28–11:48 · Nathan as informed peer 8/10 Evaluating SaaS Venture Debt Versus Equity Funding Nathan showcases strong domain knowledge around venture debt structures, disclosing his own debt investment in Badger Maps and laying out advice for negotiating founder-friendly debt terms.11:48–16:43 · Nathan as informed peer 6/10 Key Gotchas and Traps in SaaS Debt Agreements Steve delivers an in-depth breakdown of venture debt predatory clauses, including lack of business usury caps, discretionary call-backs, restrictive liquidity covenants, and prepayment penalties.16:43–19:05 · Nathan as informed peer 2/10 The Famous Five Rapid-Fire Questions Nathan runs through his standard Famous Five rapid-fire format with Steve answering thoughtfully about sleep habits and small business career development.0:56–3:51 · Guest teaching 3/10 Pandemic Impact and Exploring Healthcare Pivots Nathan frames the macro problem facing field sales during early COVID-19 lockdowns. Steve collaboratively explains the business impact and details how Badger Maps is exploring pivots into home-visit healthcare logistics.3:51–8:28 · Guest teaching 2/10 Customer Retention Tactics and Discounting Strategies Nathan asks about metrics and cancellation strategies during lockdown. Steve explains his policy of offering individual churn-risk users half off for three months while maintaining standard terms for enterprise accounts.8:28–11:48 · Guest teaching 2/10 Evaluating SaaS Venture Debt Versus Equity Funding Nathan showcases strong domain knowledge around venture debt structures, disclosing his own debt investment in Badger Maps and laying out advice for negotiating founder-friendly debt terms.11:48–16:43 · Guest teaching 8/10 Key Gotchas and Traps in SaaS Debt Agreements Steve delivers an in-depth breakdown of venture debt predatory clauses, including lack of business usury caps, discretionary call-backs, restrictive liquidity covenants, and prepayment penalties.16:43–19:05 · Guest teaching 0/10 The Famous Five Rapid-Fire Questions Nathan runs through his standard Famous Five rapid-fire format with Steve answering thoughtfully about sleep habits and small business career development.0:56–3:51 · Guest disagreement 0/10 Pandemic Impact and Exploring Healthcare Pivots Nathan frames the macro problem facing field sales during early COVID-19 lockdowns. Steve collaboratively explains the business impact and details how Badger Maps is exploring pivots into home-visit healthcare logistics.3:51–8:28 · Guest disagreement 1/10 Customer Retention Tactics and Discounting Strategies Nathan asks about metrics and cancellation strategies during lockdown. Steve explains his policy of offering individual churn-risk users half off for three months while maintaining standard terms for enterprise accounts.8:28–11:48 · Guest disagreement 0/10 Evaluating SaaS Venture Debt Versus Equity Funding Nathan showcases strong domain knowledge around venture debt structures, disclosing his own debt investment in Badger Maps and laying out advice for negotiating founder-friendly debt terms.11:48–16:43 · Guest disagreement 0/10 Key Gotchas and Traps in SaaS Debt Agreements Steve delivers an in-depth breakdown of venture debt predatory clauses, including lack of business usury caps, discretionary call-backs, restrictive liquidity covenants, and prepayment penalties.16:43–19:05 · Guest disagreement 0/10 The Famous Five Rapid-Fire Questions Nathan runs through his standard Famous Five rapid-fire format with Steve answering thoughtfully about sleep habits and small business career development.0:56–3:51 · Nathan pushing back 1/10 Pandemic Impact and Exploring Healthcare Pivots Nathan frames the macro problem facing field sales during early COVID-19 lockdowns. Steve collaboratively explains the business impact and details how Badger Maps is exploring pivots into home-visit healthcare logistics.3:51–8:28 · Nathan pushing back 2/10 Customer Retention Tactics and Discounting Strategies Nathan asks about metrics and cancellation strategies during lockdown. Steve explains his policy of offering individual churn-risk users half off for three months while maintaining standard terms for enterprise accounts.8:28–11:48 · Nathan pushing back 1/10 Evaluating SaaS Venture Debt Versus Equity Funding Nathan showcases strong domain knowledge around venture debt structures, disclosing his own debt investment in Badger Maps and laying out advice for negotiating founder-friendly debt terms.11:48–16:43 · Nathan pushing back 0/10 Key Gotchas and Traps in SaaS Debt Agreements Steve delivers an in-depth breakdown of venture debt predatory clauses, including lack of business usury caps, discretionary call-backs, restrictive liquidity covenants, and prepayment penalties.16:43–19:05 · Nathan pushing back 0/10 The Famous Five Rapid-Fire Questions Nathan runs through his standard Famous Five rapid-fire format with Steve answering thoughtfully about sleep habits and small business career development.

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

0:00 · Nathan 53.6% · guest 46.4%0:00 · Nathan 53.6% · guest 46.4%3:00 · Nathan 30.4% · guest 69.6%3:00 · Nathan 30.4% · guest 69.6%6:00 · Nathan 22.2% · guest 77.8%6:00 · Nathan 22.2% · guest 77.8%9:00 · Nathan 66% · guest 34%9:00 · Nathan 66% · guest 34%12:00 · Nathan 1.3% · guest 98.7%12:00 · Nathan 1.3% · guest 98.7%15:00 · Nathan 31.9% · guest 68.1%15:00 · Nathan 31.9% · guest 68.1%18:00 · Nathan 39.8% · guest 60.2%18:00 · Nathan 39.8% · guest 60.2%
Sharpest disagreement ▶ 4:58 Reframing focus from user count to MRR

Steve mildly rejects Nathan's focus on raw user count, clarifying that aggregate MRR is the only meaningful metric given their hybrid individual and enterprise distribution.

 Hardest push from Nathan ▶ 7:24 Pressing on software criticality during budget cuts

Nathan presses on the harsh reality of software triage, questioning whether non-essential software can actually survive when businesses cut down to the bone.

 Biggest teaching moment ▶ 13:10 Exposing illusionary liquidity covenants in SaaS lending

Steve educates the audience and host on deceptive bank covenants that lock up half the borrowed principal in restricted cash accounts.

 Nathan holds their own ▶ 10:33 Nathan lays out venture debt negotiation playbook

Nathan demonstrates high-level venture debt expertise by laying out specific tactics to eliminate prepayment penalties and bridge debt into future equity rounds.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Pandemic Impact and Exploring Healthcare Pivots 4301 Nathan frames the macro problem facing field sales during early COVID-19 lockdowns. Steve collaboratively explains the business impact and details how Badger Maps is exploring pivots into home-visit healthcare logistics.
Customer Retention Tactics and Discounting Strategies 5212 Nathan asks about metrics and cancellation strategies during lockdown. Steve explains his policy of offering individual churn-risk users half off for three months while maintaining standard terms for enterprise accounts.
Evaluating SaaS Venture Debt Versus Equity Funding 8201 Nathan showcases strong domain knowledge around venture debt structures, disclosing his own debt investment in Badger Maps and laying out advice for negotiating founder-friendly debt terms.
Key Gotchas and Traps in SaaS Debt Agreements 6800 Steve delivers an in-depth breakdown of venture debt predatory clauses, including lack of business usury caps, discretionary call-backs, restrictive liquidity covenants, and prepayment penalties.
The Famous Five Rapid-Fire Questions 2000 Nathan runs through his standard Famous Five rapid-fire format with Steve answering thoughtfully about sleep habits and small business career development.

Statements from this episode (7)

Disclosure
Benson: Badger Maps will pivot to home-visit healthcare workers
“So that's where we're going to be looking for, to pivot towards things like that and Bring in new business from that instead of to make up for the lost business in other places.”
Steve Benson Mar 20, 2020 ▶ 3:40
Assertion Not checkable as stated
Benson: Badger Maps generated about $355k MRR in March 2020
“I think we've lost about a grand in MRR so far. but The we're at about three 55 right now in MRR.”
Steve Benson Mar 20, 2020 ▶ 4:05
Assertion Not checkable as stated
Benson: Badger Maps reached 8,000 to 9,000 seats in March 2020
“Probably 8009 thousand.”
Steve Benson Mar 20, 2020 ▶ 4:23
Disclosure
Benson: Badger Maps offered 50% discounts to prevent early pandemic churn
“What we landed on was when an individual calls, we should offer them half off for three months. if they called to quit offer them half off for three months and then and then, and see if they do that instead of quitting.”
Steve Benson Mar 20, 2020 ▶ 6:28
Disclosure
Benson: Badger Maps only sold 8% equity in convertible notes
“I think we did about a. Eight percent convertible note. And this is, you know, eight, eight years ago, seven years ago, we did this. So, but no other equity other than that. So we've sold eight percent of the business in convertible notes, but no, no professio…”
Steve Benson Mar 20, 2020 ▶ 8:39
Prediction Not checkable as stated
Benson: COVID-19 disruption is definitely not a two-year problem
“This is a, this is likely a shorter term bump. Is it a three month problem? Is it an eight month problem? I'm not sure, but it's certainly not a two week problem and it's certainly not a two year problem.”
Steve Benson Mar 20, 2020 ▶ 9:46
Insight
Benson: SaaS debt interest rates drop to 16-18% above $3M revenue
“As you get larger, I think the prices come down to more around 17, 16, 17, 18%. And that's, that, I think that's much more reasonable for a more mid-sized company. You know, if you're over three million dollars, I think you could, you start creeping into that …”
Steve Benson Mar 20, 2020 ▶ 13:13
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