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May 18, 2021 · 43m · startups-for-the-rest-of-us

Episode 550 | Three Years of Grind to Six Figures in ARR with CloudForecast

Tony Chan · 20m spoken Rob Walling · 19m spoken
0:00 / 0:00
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In this episode of Startups for the Rest of Us, host Rob Walling interviews Tony Chan, co-founder of CloudForecast, exploring the three-year journey of perseverance, accelerator rejections, and strategic execution that propelled the AWS cost-monitoring platform to six figures in ARR. The discussion delivers practical insights on achieving product-market fit, navigating funding choices, and building sustainable, bootstrapped software businesses.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Rob holds 48.8% of the talking time here. How this is scored →

Rob as informed peer 3.3 Guest teaching 0.8 Guest disagreement 0.2 Rob pushing back 0.3
05100:0015:0030:002:42–11:00 · Rob as informed peer 3/10 Tony Chan's Background and the Inception of CloudForecast Rob brings up an old 2012 cold email from Tony and sets the stage for the company's inception. Tony shares the backstory warmly and collaboratively without any conflict or friction.11:00–15:10 · Rob as informed peer 4/10 Navigating the Hacker News Launch and Filtering Feedback Rob shares his experience sifting signal from noise on Hacker News launches, contrasting constructive criticism with troll feedback. Tony agrees fully and adds how they learned not to take comments personally.15:10–28:01 · Rob as informed peer 5/10 Sponsor Break: Rewardful Affiliate Marketing for SaaS Rob explains why TinySeed rejected CloudForecast initially and why they were right to turn down VC-focused programs like Launch. Tony playfully teases Rob about rejecting them twice, maintaining a friendly and reflective dynamic.28:02–34:43 · Rob as informed peer 3/10 Navigating Co-Founder Changes and Finding Product-Market Fit Tony details the difficult but amicable departure of their third co-founder and how CloudForecast evolved its product based on customer feedback. Rob asks exploring questions and Tony explains the complexity of AWS cost reporting.34:44–40:46 · Rob as informed peer 5/10 Scaling to Six Figures ARR and Effective Customer Acquisition Rob shares his evaluation criteria for founders and praises Tony and Francois for their execution and coachability. Tony reflects on the importance of founder humility and learning from past mentors.40:47–43:41 · Rob as informed peer 0/10 Listener SaaS Exit Story and Bootstrapped Community Reflections Host monologue featuring a sponsor read, an exit story from a community member, and reflections on non-traditional startup founders. No guest interaction.2:42–11:00 · Guest teaching 1/10 Tony Chan's Background and the Inception of CloudForecast Rob brings up an old 2012 cold email from Tony and sets the stage for the company's inception. Tony shares the backstory warmly and collaboratively without any conflict or friction.11:00–15:10 · Guest teaching 1/10 Navigating the Hacker News Launch and Filtering Feedback Rob shares his experience sifting signal from noise on Hacker News launches, contrasting constructive criticism with troll feedback. Tony agrees fully and adds how they learned not to take comments personally.15:10–28:01 · Guest teaching 1/10 Sponsor Break: Rewardful Affiliate Marketing for SaaS Rob explains why TinySeed rejected CloudForecast initially and why they were right to turn down VC-focused programs like Launch. Tony playfully teases Rob about rejecting them twice, maintaining a friendly and reflective dynamic.28:02–34:43 · Guest teaching 2/10 Navigating Co-Founder Changes and Finding Product-Market Fit Tony details the difficult but amicable departure of their third co-founder and how CloudForecast evolved its product based on customer feedback. Rob asks exploring questions and Tony explains the complexity of AWS cost reporting.34:44–40:46 · Guest teaching 0/10 Scaling to Six Figures ARR and Effective Customer Acquisition Rob shares his evaluation criteria for founders and praises Tony and Francois for their execution and coachability. Tony reflects on the importance of founder humility and learning from past mentors.40:47–43:41 · Guest teaching 0/10 Listener SaaS Exit Story and Bootstrapped Community Reflections Host monologue featuring a sponsor read, an exit story from a community member, and reflections on non-traditional startup founders. No guest interaction.2:42–11:00 · Guest disagreement 0/10 Tony Chan's Background and the Inception of CloudForecast Rob brings up an old 2012 cold email from Tony and sets the stage for the company's inception. Tony shares the backstory warmly and collaboratively without any conflict or friction.11:00–15:10 · Guest disagreement 0/10 Navigating the Hacker News Launch and Filtering Feedback Rob shares his experience sifting signal from noise on Hacker News launches, contrasting constructive criticism with troll feedback. Tony agrees fully and adds how they learned not to take comments personally.15:10–28:01 · Guest disagreement 1/10 Sponsor Break: Rewardful Affiliate Marketing for SaaS Rob explains why TinySeed rejected CloudForecast initially and why they were right to turn down VC-focused programs like Launch. Tony playfully teases Rob about rejecting them twice, maintaining a friendly and reflective dynamic.28:02–34:43 · Guest disagreement 0/10 Navigating Co-Founder Changes and Finding Product-Market Fit Tony details the difficult but amicable departure of their third co-founder and how CloudForecast evolved its product based on customer feedback. Rob asks exploring questions and Tony explains the complexity of AWS cost reporting.34:44–40:46 · Guest disagreement 0/10 Scaling to Six Figures ARR and Effective Customer Acquisition Rob shares his evaluation criteria for founders and praises Tony and Francois for their execution and coachability. Tony reflects on the importance of founder humility and learning from past mentors.40:47–43:41 · Guest disagreement 0/10 Listener SaaS Exit Story and Bootstrapped Community Reflections Host monologue featuring a sponsor read, an exit story from a community member, and reflections on non-traditional startup founders. No guest interaction.2:42–11:00 · Rob pushing back 0/10 Tony Chan's Background and the Inception of CloudForecast Rob brings up an old 2012 cold email from Tony and sets the stage for the company's inception. Tony shares the backstory warmly and collaboratively without any conflict or friction.11:00–15:10 · Rob pushing back 1/10 Navigating the Hacker News Launch and Filtering Feedback Rob shares his experience sifting signal from noise on Hacker News launches, contrasting constructive criticism with troll feedback. Tony agrees fully and adds how they learned not to take comments personally.15:10–28:01 · Rob pushing back 1/10 Sponsor Break: Rewardful Affiliate Marketing for SaaS Rob explains why TinySeed rejected CloudForecast initially and why they were right to turn down VC-focused programs like Launch. Tony playfully teases Rob about rejecting them twice, maintaining a friendly and reflective dynamic.28:02–34:43 · Rob pushing back 0/10 Navigating Co-Founder Changes and Finding Product-Market Fit Tony details the difficult but amicable departure of their third co-founder and how CloudForecast evolved its product based on customer feedback. Rob asks exploring questions and Tony explains the complexity of AWS cost reporting.34:44–40:46 · Rob pushing back 0/10 Scaling to Six Figures ARR and Effective Customer Acquisition Rob shares his evaluation criteria for founders and praises Tony and Francois for their execution and coachability. Tony reflects on the importance of founder humility and learning from past mentors.40:47–43:41 · Rob pushing back 0/10 Listener SaaS Exit Story and Bootstrapped Community Reflections Host monologue featuring a sponsor read, an exit story from a community member, and reflections on non-traditional startup founders. No guest interaction.

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

0:00 · Rob 91.3% · guest 8.7%0:00 · Rob 91.3% · guest 8.7%3:00 · Rob 44.9% · guest 55.1%3:00 · Rob 44.9% · guest 55.1%6:00 · Rob 69.8% · guest 30.2%6:00 · Rob 69.8% · guest 30.2%9:00 · Rob 13.8% · guest 86.2%9:00 · Rob 13.8% · guest 86.2%12:00 · Rob 52.8% · guest 47.2%12:00 · Rob 52.8% · guest 47.2%15:00 · Rob 89.5% · guest 10.5%15:00 · Rob 89.5% · guest 10.5%18:00 · Rob 4.5% · guest 95.5%18:00 · Rob 4.5% · guest 95.5%21:00 · Rob 28.4% · guest 71.6%21:00 · Rob 28.4% · guest 71.6%24:00 · Rob 35.5% · guest 64.5%24:00 · Rob 35.5% · guest 64.5%27:00 · Rob 23.2% · guest 76.8%27:00 · Rob 23.2% · guest 76.8%30:00 · Rob 39.1% · guest 60.9%30:00 · Rob 39.1% · guest 60.9%33:00 · Rob 33.5% · guest 66.5%33:00 · Rob 33.5% · guest 66.5%36:00 · Rob 47.7% · guest 52.3%36:00 · Rob 47.7% · guest 52.3%39:00 · Rob 79.8% · guest 20.2%39:00 · Rob 79.8% · guest 20.2%42:00 · Rob 100% · guest 0%42:00 · Rob 100% · guest 0%
Sharpest disagreement ▶ 24:33 Playful confrontation over rejections

Tony jokingly calls out Rob for rejecting CloudForecast twice from TinySeed when Rob notes how good of a fit they are.

 Hardest push from Rob ▶ 26:24 Explaining rejection of three co-founder setup

Rob explains his pushback against early-stage bootstrap teams with three founders, arguing money doesn't stretch far enough.

 Biggest teaching moment ▶ 32:21 Explaining the depth of AWS cost monitoring

Tony corrects Rob's assumption that cost monitoring is trivial by explaining the complexity of AWS's changing CUR file and tagging system.

 Rob holds their own ▶ 37:04 Rob detailing his criteria for founder success

Rob outlines his 40-point rubric for startup success, demonstrating deep expertise in pattern recognition across bootstrap founders.
the scores for every segment, with the reasoning behind each
ChapterTopicRob as informed peerGuest teachingGuest disagreementRob pushing backWhy
Tony Chan's Background and the Inception of CloudForecast 3100 Rob brings up an old 2012 cold email from Tony and sets the stage for the company's inception. Tony shares the backstory warmly and collaboratively without any conflict or friction.
Navigating the Hacker News Launch and Filtering Feedback 4101 Rob shares his experience sifting signal from noise on Hacker News launches, contrasting constructive criticism with troll feedback. Tony agrees fully and adds how they learned not to take comments personally.
Sponsor Break: Rewardful Affiliate Marketing for SaaS 5111 Rob explains why TinySeed rejected CloudForecast initially and why they were right to turn down VC-focused programs like Launch. Tony playfully teases Rob about rejecting them twice, maintaining a friendly and reflective dynamic.
Navigating Co-Founder Changes and Finding Product-Market Fit 3200 Tony details the difficult but amicable departure of their third co-founder and how CloudForecast evolved its product based on customer feedback. Rob asks exploring questions and Tony explains the complexity of AWS cost reporting.
Scaling to Six Figures ARR and Effective Customer Acquisition 5000 Rob shares his evaluation criteria for founders and praises Tony and Francois for their execution and coachability. Tony reflects on the importance of founder humility and learning from past mentors.
Listener SaaS Exit Story and Bootstrapped Community Reflections 0000 Host monologue featuring a sponsor read, an exit story from a community member, and reflections on non-traditional startup founders. No guest interaction.

Statements from this episode (9)

Assertion Not checkable as stated
CloudForecast reached six figures in ARR in 2020
“We passed six figures last year. And after I think working about on this about year and a half, a little bit, maybe a little bit over that we started paying ourselves.”
Tony Chan May 18, 2021 ▶ 4:30
Assertion Not checkable as stated
CloudForecast gained its first $1,000 MRR from Hacker News launch
“So half of it was just making things up as we went, but it was a very good opportunity because we did get a lot of signups and we got our first, as mentioned, 1000 dollars in MRR.”
Tony Chan May 18, 2021 ▶ 11:44
Insight
Walling: Only about 10% of negative launch feedback is valuable
“I think it's a mistake to just dismiss anything negative that comes across these, but I think there's maybe 10% of it that's actually valuable, and you really have to start considering the source at a certain point.”
Rob Walling May 18, 2021 ▶ 14:08
Assertion Not checkable as stated
CloudForecast turned down LAUNCH after multiple accelerator rejections in 2018–2019
“So let's go through YC interviewed for YC in 2018 rejected interviewed for tiny seed 2019 rejected applied interviewed For Indie.VC, Ernest Capital, Techstars, Chicago, and Boulder rejected. But in 2019 as well, you applied and interviewed for launch, and you …”
Rob Walling May 18, 2021 ▶ 16:57
Disclosure
CloudForecast declined LAUNCH accelerator's offer over its focus on venture scale
“We interviewed for launch and we got the offer. It was something that we had to talk about because if we went to launch and if you know, Jason Calacanis, he's all about building unicorns and Going through the venture route. And as we learned a little bit more …”
Tony Chan May 18, 2021 ▶ 22:02
Insight
Walling: Bootstrapped startups with 3 or 4 co-founders have one too many
“Oftentimes when I see bootstrapped or mostly bootstrap companies with three or four co-founders, usually they're too many. Usually there's at least one too many and there's like a weak link. There's someone who's not Maybe holding up there”
Rob Walling May 18, 2021 ▶ 26:25
Opinion
Chan: AWS has no incentive to help customers save money
“I don't think they have the incentive of helping people save money.”
Tony Chan May 18, 2021 ▶ 34:01
Insight
Walling: Early-Stage Startup Success Comes Down to People, PMF, and Pricing
“Of course, I have this big long list in, in a Google doc of all the criteria. It's like 40 something criteria, but really the top line thing is people, product market fit, and pricing or price sensitivity.”
Rob Walling May 18, 2021 ▶ 37:26
Assertion Contradicted
Walling: 80% to 90% of VC goes to Harvard or Stanford alumni
“In fact, I saw a number somewhere and it was about, it was like 80% or 90% of venture capital goes to someone who graduated from Harvard or Stanford, or at least someone who attended one of those schools.”
Rob Walling May 18, 2021 ▶ 42:22
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