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Aug 10, 2020 · 22m · top-founders

BillBooks Invoicing Tool Hits 5,000 Paying Customers, Bootstrapped

Sagar Kokakar · 11m spoken Nathan Latka · 8m spoken
0:00 / 0:00

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In this episode of Conversations with Nathan Latka, host Nathan Latka interviews Billbooks founder Sagar Kokakar to dissect the unit economics, pricing migration, and marketing funnel of a bootstrapped invoicing platform generating 75,000 dollars per month.

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 41.7% of the talking time here. How this is scored →

Nathan as informed peer 6.6 Guest teaching 2.9 Guest disagreement 2.6 Nathan pushing back 6.4
05100:0010:0020:000:00–4:10 · Nathan as informed peer 4/10 Episode Hook: Billbooks User Base Discussion Nathan introduces the guest and inquires into Billbooks' origin story and team setup. The dynamic is conversational and straightforward as Kokakar outlines his background running an agency and building the tool bootstrapped with a 5-person team.4:11–7:11 · Nathan as informed peer 7/10 Early Customers, SEO Channels, and Pricing Evolution Nathan demonstrates domain expertise by pulling up live Ahrefs SEO metrics, challenging Kokakar on his low Domain Rating of 33 and URL Rating of 36. Kokakar explains their pivot from pay-per-invoice pricing to subscription plans amid increasing competition.7:12–9:34 · Nathan as informed peer 6/10 Marketing Strategies, Trial Funnel, and Feature Gaps Nathan pushes Kokakar on customer acquisition numbers, immediately clarifying that 50 daily trials do not equate to customers and calling out a 1-3% conversion rate as exceptionally weak. Kokakar candidly admits feature gaps like missing bank reconciliations compared to FreshBooks.9:35–13:00 · Nathan as informed peer 8/10 Clarifying Paying Customer Base vs Historical Accounts Kokakar attempts to dodge disclosing customer numbers under the guise of marketing strategy, before claiming 50k paying users. Nathan dismantles the claim by calculating that 50k users at $15/month would yield $10M ARR, forcing Kokakar to admit only 5k-8k are actual monthly paying subscribers.13:05–17:56 · Nathan as informed peer 7/10 Sponsor Segment: Freelance Talent Sourcing via Fiverr After an ad break, Kokakar asks Nathan to edit out the revenue disclosure, but Nathan firmly refuses, reiterating show policy and distinguishing historical pay-per-use users from active subscribers. Nathan also questions whether heavy discounting is a healthy long-term conversion tactic.17:56–20:21 · Nathan as informed peer 6/10 Profit Margins, Research, and Market Competition Nathan presses for net profit percentages and asks why competitors like FreshBooks outpaced Billbooks despite launching later. Kokakar provides an insightful explanation, admitting his mistake of sticking with the pay-per-invoice model too long while venture-backed rivals scaled.20:22–22:27 · Nathan as informed peer 8/10 Acquisition Funnel, Search Volume, and Monthly Retention Nathan catches Kokakar in a mathematical contradiction regarding daily trial counts versus monthly totals and organic traffic volume (640 clicks/month). When Nathan inquires about monthly churn, Kokakar confuses trial drop-off with paid churn and improbably claims zero churn.0:00–4:10 · Guest teaching 2/10 Episode Hook: Billbooks User Base Discussion Nathan introduces the guest and inquires into Billbooks' origin story and team setup. The dynamic is conversational and straightforward as Kokakar outlines his background running an agency and building the tool bootstrapped with a 5-person team.4:11–7:11 · Guest teaching 3/10 Early Customers, SEO Channels, and Pricing Evolution Nathan demonstrates domain expertise by pulling up live Ahrefs SEO metrics, challenging Kokakar on his low Domain Rating of 33 and URL Rating of 36. Kokakar explains their pivot from pay-per-invoice pricing to subscription plans amid increasing competition.7:12–9:34 · Guest teaching 4/10 Marketing Strategies, Trial Funnel, and Feature Gaps Nathan pushes Kokakar on customer acquisition numbers, immediately clarifying that 50 daily trials do not equate to customers and calling out a 1-3% conversion rate as exceptionally weak. Kokakar candidly admits feature gaps like missing bank reconciliations compared to FreshBooks.9:35–13:00 · Guest teaching 2/10 Clarifying Paying Customer Base vs Historical Accounts Kokakar attempts to dodge disclosing customer numbers under the guise of marketing strategy, before claiming 50k paying users. Nathan dismantles the claim by calculating that 50k users at $15/month would yield $10M ARR, forcing Kokakar to admit only 5k-8k are actual monthly paying subscribers.13:05–17:56 · Guest teaching 2/10 Sponsor Segment: Freelance Talent Sourcing via Fiverr After an ad break, Kokakar asks Nathan to edit out the revenue disclosure, but Nathan firmly refuses, reiterating show policy and distinguishing historical pay-per-use users from active subscribers. Nathan also questions whether heavy discounting is a healthy long-term conversion tactic.17:56–20:21 · Guest teaching 5/10 Profit Margins, Research, and Market Competition Nathan presses for net profit percentages and asks why competitors like FreshBooks outpaced Billbooks despite launching later. Kokakar provides an insightful explanation, admitting his mistake of sticking with the pay-per-invoice model too long while venture-backed rivals scaled.20:22–22:27 · Guest teaching 2/10 Acquisition Funnel, Search Volume, and Monthly Retention Nathan catches Kokakar in a mathematical contradiction regarding daily trial counts versus monthly totals and organic traffic volume (640 clicks/month). When Nathan inquires about monthly churn, Kokakar confuses trial drop-off with paid churn and improbably claims zero churn.0:00–4:10 · Guest disagreement 1/10 Episode Hook: Billbooks User Base Discussion Nathan introduces the guest and inquires into Billbooks' origin story and team setup. The dynamic is conversational and straightforward as Kokakar outlines his background running an agency and building the tool bootstrapped with a 5-person team.4:11–7:11 · Guest disagreement 2/10 Early Customers, SEO Channels, and Pricing Evolution Nathan demonstrates domain expertise by pulling up live Ahrefs SEO metrics, challenging Kokakar on his low Domain Rating of 33 and URL Rating of 36. Kokakar explains their pivot from pay-per-invoice pricing to subscription plans amid increasing competition.7:12–9:34 · Guest disagreement 2/10 Marketing Strategies, Trial Funnel, and Feature Gaps Nathan pushes Kokakar on customer acquisition numbers, immediately clarifying that 50 daily trials do not equate to customers and calling out a 1-3% conversion rate as exceptionally weak. Kokakar candidly admits feature gaps like missing bank reconciliations compared to FreshBooks.9:35–13:00 · Guest disagreement 4/10 Clarifying Paying Customer Base vs Historical Accounts Kokakar attempts to dodge disclosing customer numbers under the guise of marketing strategy, before claiming 50k paying users. Nathan dismantles the claim by calculating that 50k users at $15/month would yield $10M ARR, forcing Kokakar to admit only 5k-8k are actual monthly paying subscribers.13:05–17:56 · Guest disagreement 4/10 Sponsor Segment: Freelance Talent Sourcing via Fiverr After an ad break, Kokakar asks Nathan to edit out the revenue disclosure, but Nathan firmly refuses, reiterating show policy and distinguishing historical pay-per-use users from active subscribers. Nathan also questions whether heavy discounting is a healthy long-term conversion tactic.17:56–20:21 · Guest disagreement 2/10 Profit Margins, Research, and Market Competition Nathan presses for net profit percentages and asks why competitors like FreshBooks outpaced Billbooks despite launching later. Kokakar provides an insightful explanation, admitting his mistake of sticking with the pay-per-invoice model too long while venture-backed rivals scaled.20:22–22:27 · Guest disagreement 3/10 Acquisition Funnel, Search Volume, and Monthly Retention Nathan catches Kokakar in a mathematical contradiction regarding daily trial counts versus monthly totals and organic traffic volume (640 clicks/month). When Nathan inquires about monthly churn, Kokakar confuses trial drop-off with paid churn and improbably claims zero churn.0:00–4:10 · Nathan pushing back 2/10 Episode Hook: Billbooks User Base Discussion Nathan introduces the guest and inquires into Billbooks' origin story and team setup. The dynamic is conversational and straightforward as Kokakar outlines his background running an agency and building the tool bootstrapped with a 5-person team.4:11–7:11 · Nathan pushing back 6/10 Early Customers, SEO Channels, and Pricing Evolution Nathan demonstrates domain expertise by pulling up live Ahrefs SEO metrics, challenging Kokakar on his low Domain Rating of 33 and URL Rating of 36. Kokakar explains their pivot from pay-per-invoice pricing to subscription plans amid increasing competition.7:12–9:34 · Nathan pushing back 6/10 Marketing Strategies, Trial Funnel, and Feature Gaps Nathan pushes Kokakar on customer acquisition numbers, immediately clarifying that 50 daily trials do not equate to customers and calling out a 1-3% conversion rate as exceptionally weak. Kokakar candidly admits feature gaps like missing bank reconciliations compared to FreshBooks.9:35–13:00 · Nathan pushing back 9/10 Clarifying Paying Customer Base vs Historical Accounts Kokakar attempts to dodge disclosing customer numbers under the guise of marketing strategy, before claiming 50k paying users. Nathan dismantles the claim by calculating that 50k users at $15/month would yield $10M ARR, forcing Kokakar to admit only 5k-8k are actual monthly paying subscribers.13:05–17:56 · Nathan pushing back 8/10 Sponsor Segment: Freelance Talent Sourcing via Fiverr After an ad break, Kokakar asks Nathan to edit out the revenue disclosure, but Nathan firmly refuses, reiterating show policy and distinguishing historical pay-per-use users from active subscribers. Nathan also questions whether heavy discounting is a healthy long-term conversion tactic.17:56–20:21 · Nathan pushing back 6/10 Profit Margins, Research, and Market Competition Nathan presses for net profit percentages and asks why competitors like FreshBooks outpaced Billbooks despite launching later. Kokakar provides an insightful explanation, admitting his mistake of sticking with the pay-per-invoice model too long while venture-backed rivals scaled.20:22–22:27 · Nathan pushing back 8/10 Acquisition Funnel, Search Volume, and Monthly Retention Nathan catches Kokakar in a mathematical contradiction regarding daily trial counts versus monthly totals and organic traffic volume (640 clicks/month). When Nathan inquires about monthly churn, Kokakar confuses trial drop-off with paid churn and improbably claims zero churn.

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

0:00 · Nathan 57.5% · guest 42.5%0:00 · Nathan 57.5% · guest 42.5%3:00 · Nathan 27.1% · guest 72.9%3:00 · Nathan 27.1% · guest 72.9%6:00 · Nathan 23.9% · guest 76.1%6:00 · Nathan 23.9% · guest 76.1%9:00 · Nathan 20.3% · guest 79.7%9:00 · Nathan 20.3% · guest 79.7%12:00 · Nathan 77.5% · guest 22.5%12:00 · Nathan 77.5% · guest 22.5%15:00 · Nathan 53.9% · guest 46.1%15:00 · Nathan 53.9% · guest 46.1%18:00 · Nathan 27.5% · guest 72.5%18:00 · Nathan 27.5% · guest 72.5%21:00 · Nathan 45.3% · guest 54.7%21:00 · Nathan 45.3% · guest 54.7%
Sharpest disagreement ▶ 10:05 Refusing to disclose customer metrics over marketing concerns

Kokakar resists Nathan's questioning by claiming disclosure of customer counts would prejudice prospective customers across regional marketing campaigns.

 Hardest push from Nathan ▶ 15:10 Nathan refuses to edit out financial disclosures

When Kokakar asks to cut out the revenue figures, Nathan firmly shuts down the request and explains the necessity of keeping the data on record.

 Biggest teaching moment ▶ 19:32 Admitting legacy pricing model mistake against funded competitors

Kokakar educates Nathan on how lingering on a transactional per-invoice pricing model stymied company growth compared to venture-backed subscription rivals.

 Nathan holds their own ▶ 12:14 Exposing inflated subscriber math

Nathan instantly calculates that 50,000 users at $15/month implies $9M+ in ARR, disproving Kokakar's claim and forcing him to lower his count to 5,000 subscribers.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Episode Hook: Billbooks User Base Discussion 4212 Nathan introduces the guest and inquires into Billbooks' origin story and team setup. The dynamic is conversational and straightforward as Kokakar outlines his background running an agency and building the tool bootstrapped with a 5-person team.
Early Customers, SEO Channels, and Pricing Evolution 7326 Nathan demonstrates domain expertise by pulling up live Ahrefs SEO metrics, challenging Kokakar on his low Domain Rating of 33 and URL Rating of 36. Kokakar explains their pivot from pay-per-invoice pricing to subscription plans amid increasing competition.
Marketing Strategies, Trial Funnel, and Feature Gaps 6426 Nathan pushes Kokakar on customer acquisition numbers, immediately clarifying that 50 daily trials do not equate to customers and calling out a 1-3% conversion rate as exceptionally weak. Kokakar candidly admits feature gaps like missing bank reconciliations compared to FreshBooks.
Clarifying Paying Customer Base vs Historical Accounts 8249 Kokakar attempts to dodge disclosing customer numbers under the guise of marketing strategy, before claiming 50k paying users. Nathan dismantles the claim by calculating that 50k users at $15/month would yield $10M ARR, forcing Kokakar to admit only 5k-8k are actual monthly paying subscribers.
Sponsor Segment: Freelance Talent Sourcing via Fiverr 7248 After an ad break, Kokakar asks Nathan to edit out the revenue disclosure, but Nathan firmly refuses, reiterating show policy and distinguishing historical pay-per-use users from active subscribers. Nathan also questions whether heavy discounting is a healthy long-term conversion tactic.
Profit Margins, Research, and Market Competition 6526 Nathan presses for net profit percentages and asks why competitors like FreshBooks outpaced Billbooks despite launching later. Kokakar provides an insightful explanation, admitting his mistake of sticking with the pay-per-invoice model too long while venture-backed rivals scaled.
Acquisition Funnel, Search Volume, and Monthly Retention 8238 Nathan catches Kokakar in a mathematical contradiction regarding daily trial counts versus monthly totals and organic traffic volume (640 clicks/month). When Nathan inquires about monthly churn, Kokakar confuses trial drop-off with paid churn and improbably claims zero churn.

Statements from this episode (12)

Disclosure
Kokakar: Billbooks' development was funded internally by his digital agency
“I had a digital agency which was internally funding this product.”
Sagar Kokakar Aug 10, 2020 ▶ 3:19
Assertion Not checkable as stated
Kokakar: Billbooks operates with a lean team of just five people
“We're just five.”
Sagar Kokakar Aug 10, 2020 ▶ 3:41
Disclosure
Kokakar: Billbooks launched in 2011 charging $0.50 per invoice sent
“The initial books you mentioned about the revenue model the key was to keep it very economical, and it was a pay-per-use model, so we used to charge 50 cents per invoice sent when we launched back in 2011, instead of per user per month.”
Sagar Kokakar Aug 10, 2020 ▶ 6:25
Disclosure
Kokakar: Billbooks plans run $7.95–$29.95/mo, ARPU is $15–$20
“So our plans start from about seven 95 and they go on to about 29 95. It's still below the market price at the moment and an average customer would spend anywhere between 15 and 20 dollars.”
Sagar Kokakar Aug 10, 2020 ▶ 6:56
Assertion Not checkable as stated
Kokakar: Billbooks converts 1% to 3% of free trials to paid
“It really depends, but like a typical it's an average SAS based. So it's one anywhere between one and three percent.”
Sagar Kokakar Aug 10, 2020 ▶ 8:34
Opinion
Kokakar: Billbooks lacks bank reconciliation features compared to competitors
“So we're still lagging behind on, on a few features, I feel, and that could be, possibly be the differentiators between us and the competition.”
Sagar Kokakar Aug 10, 2020 ▶ 9:25
Assertion Not checkable as stated
Kokakar: Billbooks has between 50,000 and 100,000 total paying customers
“Total, I mean I can give you a range anywhere between, you know, 50 and a 100,000, so it can't, you know, it wouldn't go anywhere beyond that.”
Sagar Kokakar Aug 10, 2020 ▶ 12:04
Assertion Not checkable as stated
Kokakar: Billbooks has 5,000 to 8,000 monthly subscription customers
“On the monthly subscription plan would be probably anywhere between five and 8000, yeah.”
Sagar Kokakar Aug 10, 2020 ▶ 12:55
Disclosure
Kokakar: Billbooks does not intend to raise outside funding
“I, yeah, we do not intend to raise money for bill books going forward. Hopefully I mean, never say never, but we've got a very firm kind of goal structure the product development structure that we have in place. And we kind of, we know that where we want to go…”
Sagar Kokakar Aug 10, 2020 ▶ 17:23
Assertion Not checkable as stated
Kokakar: Billbooks maintains a 30% to 40% net profit margin
“About 30 to 40%.”
Sagar Kokakar Aug 10, 2020 ▶ 18:26
Prediction Open · timeframe Dec 2027
Kokakar: 50.9% of Americans will probably freelance by 2027
“Like for instance freelancing by 20, 27 about more majority, 50.9% of the Americans would probably venture into freelancing.”
Sagar Kokakar Aug 10, 2020 ▶ 18:41
Assertion Not checkable as stated
Kokakar: Billbooks adds 400 to 500 trial signups per month
“In a month, you could say anywhere between about, ah, four to 500.”
Sagar Kokakar Aug 10, 2020 ▶ 20:45
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