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Jul 28, 2017 · 22m · 20vc

20VC: Construct Your Fundraising Process To Get 3 Term Sheets in 36 Hours, Why Slow and Steady Can Be Best For Startups & Why All Startups Must Know Their Zero Cash Day with Nathan Wenzel, Founder & CEO @ SimpleLegal

Nathan Wenzel · 13m spoken Harry Stebbings · 8m spoken
0:00 / 0:00

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

In this episode of The 20 Minute VC, Nathan Wenzel, Founder and CEO of Simple Legal, discusses his disciplined approach to enterprise SaaS growth, sharing insights on burn rate management, achieving product-market fit, and executing a Series A fundraising process that secured three term sheets in 36 hours.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 39.2% of the talking time here. How this is scored →

Harry as informed peer 2.6 Guest teaching 3.0 Guest disagreement 1.0 Harry pushing back 1.6
05100:0010:0020:002:23–4:38 · Harry as informed peer 1/10 Transitioning from Consulting Services to Enterprise SaaS Harry opens with standard biographical questions about Nathan's background and transition from consulting to enterprise software. Nathan politely describes the early operational friction of retraining enterprise consulting clients to buy standardized SaaS.4:45–9:27 · Harry as informed peer 3/10 Rethinking Startup Growth: The Case for Slow and Steady Harry contrasts Nathan's slow and steady growth approach against the traditional VC playbook of aggressive hiring and burn. Nathan reframes growth in enterprise SaaS around customer retention, low churn, and product market fit over raw velocity.9:29–12:34 · Harry as informed peer 3/10 Navigating Market Corrections, Burn Rates, and Profitability Harry prompts Nathan on his tweet regarding market downturns and Bay Area burn rates. Nathan offers a sober critique of venture-backed burn rates, arguing that founders must track their profitability day alongside zero cash day.12:41–17:33 · Harry as informed peer 4/10 Designing a Series A Strategy: 3 Term Sheets in 36 Hours Harry asks Nathan to breakdown his disciplined Series A strategy that yielded three term sheets in 36 hours. Harry demonstrates good industry knowledge regarding VC negotiation leverage and sales motion alignment.17:38–20:41 · Harry as informed peer 2/10 Quick-Fire Insights: Startup Myths, Hiring, and Future Outlook In the quick-fire segment, Nathan explicitly rejects the popular startup trope of 'hire fast, fire fast'. Harry facilitates with brief follow-ups on hiring timelines for specific roles.2:23–4:38 · Guest teaching 2/10 Transitioning from Consulting Services to Enterprise SaaS Harry opens with standard biographical questions about Nathan's background and transition from consulting to enterprise software. Nathan politely describes the early operational friction of retraining enterprise consulting clients to buy standardized SaaS.4:45–9:27 · Guest teaching 3/10 Rethinking Startup Growth: The Case for Slow and Steady Harry contrasts Nathan's slow and steady growth approach against the traditional VC playbook of aggressive hiring and burn. Nathan reframes growth in enterprise SaaS around customer retention, low churn, and product market fit over raw velocity.9:29–12:34 · Guest teaching 4/10 Navigating Market Corrections, Burn Rates, and Profitability Harry prompts Nathan on his tweet regarding market downturns and Bay Area burn rates. Nathan offers a sober critique of venture-backed burn rates, arguing that founders must track their profitability day alongside zero cash day.12:41–17:33 · Guest teaching 3/10 Designing a Series A Strategy: 3 Term Sheets in 36 Hours Harry asks Nathan to breakdown his disciplined Series A strategy that yielded three term sheets in 36 hours. Harry demonstrates good industry knowledge regarding VC negotiation leverage and sales motion alignment.17:38–20:41 · Guest teaching 3/10 Quick-Fire Insights: Startup Myths, Hiring, and Future Outlook In the quick-fire segment, Nathan explicitly rejects the popular startup trope of 'hire fast, fire fast'. Harry facilitates with brief follow-ups on hiring timelines for specific roles.2:23–4:38 · Guest disagreement 0/10 Transitioning from Consulting Services to Enterprise SaaS Harry opens with standard biographical questions about Nathan's background and transition from consulting to enterprise software. Nathan politely describes the early operational friction of retraining enterprise consulting clients to buy standardized SaaS.4:45–9:27 · Guest disagreement 1/10 Rethinking Startup Growth: The Case for Slow and Steady Harry contrasts Nathan's slow and steady growth approach against the traditional VC playbook of aggressive hiring and burn. Nathan reframes growth in enterprise SaaS around customer retention, low churn, and product market fit over raw velocity.9:29–12:34 · Guest disagreement 2/10 Navigating Market Corrections, Burn Rates, and Profitability Harry prompts Nathan on his tweet regarding market downturns and Bay Area burn rates. Nathan offers a sober critique of venture-backed burn rates, arguing that founders must track their profitability day alongside zero cash day.12:41–17:33 · Guest disagreement 0/10 Designing a Series A Strategy: 3 Term Sheets in 36 Hours Harry asks Nathan to breakdown his disciplined Series A strategy that yielded three term sheets in 36 hours. Harry demonstrates good industry knowledge regarding VC negotiation leverage and sales motion alignment.17:38–20:41 · Guest disagreement 2/10 Quick-Fire Insights: Startup Myths, Hiring, and Future Outlook In the quick-fire segment, Nathan explicitly rejects the popular startup trope of 'hire fast, fire fast'. Harry facilitates with brief follow-ups on hiring timelines for specific roles.2:23–4:38 · Harry pushing back 0/10 Transitioning from Consulting Services to Enterprise SaaS Harry opens with standard biographical questions about Nathan's background and transition from consulting to enterprise software. Nathan politely describes the early operational friction of retraining enterprise consulting clients to buy standardized SaaS.4:45–9:27 · Harry pushing back 3/10 Rethinking Startup Growth: The Case for Slow and Steady Harry contrasts Nathan's slow and steady growth approach against the traditional VC playbook of aggressive hiring and burn. Nathan reframes growth in enterprise SaaS around customer retention, low churn, and product market fit over raw velocity.9:29–12:34 · Harry pushing back 2/10 Navigating Market Corrections, Burn Rates, and Profitability Harry prompts Nathan on his tweet regarding market downturns and Bay Area burn rates. Nathan offers a sober critique of venture-backed burn rates, arguing that founders must track their profitability day alongside zero cash day.12:41–17:33 · Harry pushing back 1/10 Designing a Series A Strategy: 3 Term Sheets in 36 Hours Harry asks Nathan to breakdown his disciplined Series A strategy that yielded three term sheets in 36 hours. Harry demonstrates good industry knowledge regarding VC negotiation leverage and sales motion alignment.17:38–20:41 · Harry pushing back 2/10 Quick-Fire Insights: Startup Myths, Hiring, and Future Outlook In the quick-fire segment, Nathan explicitly rejects the popular startup trope of 'hire fast, fire fast'. Harry facilitates with brief follow-ups on hiring timelines for specific roles.

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

0:00 · Harry 91.5% · guest 8.5%0:00 · Harry 91.5% · guest 8.5%3:00 · Harry 20.1% · guest 79.9%3:00 · Harry 20.1% · guest 79.9%6:00 · Harry 23.7% · guest 76.3%6:00 · Harry 23.7% · guest 76.3%9:00 · Harry 17.5% · guest 82.5%9:00 · Harry 17.5% · guest 82.5%12:00 · Harry 32.7% · guest 67.3%12:00 · Harry 32.7% · guest 67.3%15:00 · Harry 22.6% · guest 77.4%15:00 · Harry 22.6% · guest 77.4%18:00 · Harry 31.4% · guest 68.6%18:00 · Harry 31.4% · guest 68.6%21:00 · Harry 100% · guest 0%21:00 · Harry 100% · guest 0%
Sharpest disagreement ▶ 19:14 Rejecting the hire fast fire fast adage

Nathan directly rejects Harry's quick-fire premise about hiring velocity, arguing instead that a manager's primary job is to enable team success through patient hiring.

 Hardest push from Harry ▶ 11:18 Challenging market downturn predictions

Harry explicitly presses Nathan on his tweet about impending market corrections, asking for specific justification behind his macro prediction.

 Biggest teaching moment ▶ 10:39 Expanding the zero cash day concept to profitability

Nathan reframes standard startup cash management wisdom by showing how tracking profitability day gives founders control over burn rates during downturns.

 Harry holds his own ▶ 15:50 Analyzing venture leverage in fundraising

Harry clearly demonstrates his grasp of VC dynamics by pointing out how capital constraints give investors leverage over valuation and timing during rounds.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Transitioning from Consulting Services to Enterprise SaaS 1200 Harry opens with standard biographical questions about Nathan's background and transition from consulting to enterprise software. Nathan politely describes the early operational friction of retraining enterprise consulting clients to buy standardized SaaS.
Rethinking Startup Growth: The Case for Slow and Steady 3313 Harry contrasts Nathan's slow and steady growth approach against the traditional VC playbook of aggressive hiring and burn. Nathan reframes growth in enterprise SaaS around customer retention, low churn, and product market fit over raw velocity.
Navigating Market Corrections, Burn Rates, and Profitability 3422 Harry prompts Nathan on his tweet regarding market downturns and Bay Area burn rates. Nathan offers a sober critique of venture-backed burn rates, arguing that founders must track their profitability day alongside zero cash day.
Designing a Series A Strategy: 3 Term Sheets in 36 Hours 4301 Harry asks Nathan to breakdown his disciplined Series A strategy that yielded three term sheets in 36 hours. Harry demonstrates good industry knowledge regarding VC negotiation leverage and sales motion alignment.
Quick-Fire Insights: Startup Myths, Hiring, and Future Outlook 2322 In the quick-fire segment, Nathan explicitly rejects the popular startup trope of 'hire fast, fire fast'. Harry facilitates with brief follow-ups on hiring timelines for specific roles.

Statements from this episode (8)

Disclosure
SimpleLegal Waited Two Years Before Hiring Its First Employee
“We spent 18 months to get it right, but once we saw that it was working, we took another six months before we hired our first employee”
Nathan Wenzel Jul 28, 2017 ▶ 5:46
Insight
"Move Fast and Break Things" Fails for SOX-Compliant SaaS Startups
“The idea of move fast and break things really doesn't work if you need to be SOX compliant, and if you're asking your customers to trust you with their financials.”
Nathan Wenzel Jul 28, 2017 ▶ 6:11
Disclosure
SimpleLegal Maintained Near-Zero Gross Churn During Early Growth
“Our gross churn was near zero.”
Nathan Wenzel Jul 28, 2017 ▶ 8:20
Opinion
Relying on Continuous VC Funding Availability Is Dangerous for Startups
“VC money is just always around the corner, and if you need more money, you just go and ask for it. It's a dangerous assumption to make, and we've already seen companies that have raised tens of millions of dollars just disappear overnight because they thought …”
Nathan Wenzel Jul 28, 2017 ▶ 10:13
Disclosure
SimpleLegal Maintained Near-Zero Company Net Burn for Its First 18 Months
“For us, we were net zero burn for the first year and a half. Our personal burn rates were not net zero, but our company net burn was near zero.”
Nathan Wenzel Jul 28, 2017 ▶ 10:40
What-if
SimpleLegal Would Have Reached Profitability by Q3 2017 Without Series A
“Had we chosen not to raise money, we would have been profitable by the beginning of the third quarter.”
Nathan Wenzel Jul 28, 2017 ▶ 15:35
Disclosure
Leo Polovets Made a Personal Angel Investment in SimpleLegal
“One of the partners saw something in us, and so he made a personal investment. And so that was Leo Polovets from Sousa Ventures.”
Nathan Wenzel Jul 28, 2017 ▶ 16:51
Assertion Supported
Y Combinator Is Not Just for 22-Year-Olds, Says 35-Year-Old Alum
“We went through, I was 35 at the time, and I was not the oldest. So I think the idea that YC is really just for twenty-two-year-olds is, is kind of a myth.”
Nathan Wenzel Jul 28, 2017 ▶ 18:33
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