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Jun 13, 2023 · 21m · startup-acquisition-stories

Startup Acquisition Stories with Ruslan Leteyski, Founder & CEO of Checkout X

Ruslan Leteyski · 13m spoken Andrew Gazdecki · 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

In this episode of Startup Acquisition Stories, host Andrew Gazdecki interviews Ruslan Leteyski, founder of Vanga AI and Checkout X, about building, scaling, and successfully exiting his automated Shopify upselling application on Acquire.com. Ruslan shares candid insights on navigating platform competition, preparing a digital asset sale, selecting the right strategic buyer, and optimizing SaaS valuation metrics for an exit.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Andrew holds 30.1% of the talking time here. How this is scored →

Andrew as informed peer 4.0 Guest teaching 2.5 Guest disagreement 0.3 Andrew pushing back 0.2
05100:0010:0020:000:24–4:00 · Andrew as informed peer 3/10 Introducing Ruslan Leteyski and Vanga AI A friendly opening where Ruslan playfully notes he preferred the company's old name MicroAcquire. Andrew politely clarifies the rationale behind dropping 'micro' before asking about Vanga AI's background and early traction.4:00–6:10 · Andrew as informed peer 3/10 Deciding to Sell in a Competitive Market Ruslan transparently details the fierce competition in the Shopify upsell niche that motivated the sale. Andrew affirms Ruslan's self-awareness in choosing to exit cleanly.6:10–8:28 · Andrew as informed peer 4/10 Preparation and Listing Strategy on Acquire.com Ruslan shares his proactive approach to asset separation and listing documentation. Andrew reinforces how essential comprehensive upfront preparation is to deal success.8:28–12:46 · Andrew as informed peer 6/10 Evaluating Buyer Interest and Selecting the Right Partner Ruslan explains why he preferred an experienced acquirer over higher-bidding novices. Andrew displays clear marketplace expertise, elaborating on pre-due diligence and why veteran buyers close at higher rates.12:46–16:56 · Andrew as informed peer 4/10 Due Diligence Hurdles and Asset Transfer Execution Ruslan describes practical bottlenecks during due diligence and asset handover, including codebase vulnerability and a midnight server crash. Andrew empathizes with the operational hiccups.16:56–20:08 · Andrew as informed peer 4/10 Key Learnings, Marketplace Liquidity, and Seller Advice Ruslan offers strategic advice on SaaS exits, highlighting the valuation gap between pure recurring revenue and usage-based models. Andrew validates the insights and supports the unique liquidity of Shopify apps.0:24–4:00 · Guest teaching 2/10 Introducing Ruslan Leteyski and Vanga AI A friendly opening where Ruslan playfully notes he preferred the company's old name MicroAcquire. Andrew politely clarifies the rationale behind dropping 'micro' before asking about Vanga AI's background and early traction.4:00–6:10 · Guest teaching 2/10 Deciding to Sell in a Competitive Market Ruslan transparently details the fierce competition in the Shopify upsell niche that motivated the sale. Andrew affirms Ruslan's self-awareness in choosing to exit cleanly.6:10–8:28 · Guest teaching 2/10 Preparation and Listing Strategy on Acquire.com Ruslan shares his proactive approach to asset separation and listing documentation. Andrew reinforces how essential comprehensive upfront preparation is to deal success.8:28–12:46 · Guest teaching 2/10 Evaluating Buyer Interest and Selecting the Right Partner Ruslan explains why he preferred an experienced acquirer over higher-bidding novices. Andrew displays clear marketplace expertise, elaborating on pre-due diligence and why veteran buyers close at higher rates.12:46–16:56 · Guest teaching 3/10 Due Diligence Hurdles and Asset Transfer Execution Ruslan describes practical bottlenecks during due diligence and asset handover, including codebase vulnerability and a midnight server crash. Andrew empathizes with the operational hiccups.16:56–20:08 · Guest teaching 4/10 Key Learnings, Marketplace Liquidity, and Seller Advice Ruslan offers strategic advice on SaaS exits, highlighting the valuation gap between pure recurring revenue and usage-based models. Andrew validates the insights and supports the unique liquidity of Shopify apps.0:24–4:00 · Guest disagreement 1/10 Introducing Ruslan Leteyski and Vanga AI A friendly opening where Ruslan playfully notes he preferred the company's old name MicroAcquire. Andrew politely clarifies the rationale behind dropping 'micro' before asking about Vanga AI's background and early traction.4:00–6:10 · Guest disagreement 0/10 Deciding to Sell in a Competitive Market Ruslan transparently details the fierce competition in the Shopify upsell niche that motivated the sale. Andrew affirms Ruslan's self-awareness in choosing to exit cleanly.6:10–8:28 · Guest disagreement 0/10 Preparation and Listing Strategy on Acquire.com Ruslan shares his proactive approach to asset separation and listing documentation. Andrew reinforces how essential comprehensive upfront preparation is to deal success.8:28–12:46 · Guest disagreement 0/10 Evaluating Buyer Interest and Selecting the Right Partner Ruslan explains why he preferred an experienced acquirer over higher-bidding novices. Andrew displays clear marketplace expertise, elaborating on pre-due diligence and why veteran buyers close at higher rates.12:46–16:56 · Guest disagreement 1/10 Due Diligence Hurdles and Asset Transfer Execution Ruslan describes practical bottlenecks during due diligence and asset handover, including codebase vulnerability and a midnight server crash. Andrew empathizes with the operational hiccups.16:56–20:08 · Guest disagreement 0/10 Key Learnings, Marketplace Liquidity, and Seller Advice Ruslan offers strategic advice on SaaS exits, highlighting the valuation gap between pure recurring revenue and usage-based models. Andrew validates the insights and supports the unique liquidity of Shopify apps.0:24–4:00 · Andrew pushing back 1/10 Introducing Ruslan Leteyski and Vanga AI A friendly opening where Ruslan playfully notes he preferred the company's old name MicroAcquire. Andrew politely clarifies the rationale behind dropping 'micro' before asking about Vanga AI's background and early traction.4:00–6:10 · Andrew pushing back 0/10 Deciding to Sell in a Competitive Market Ruslan transparently details the fierce competition in the Shopify upsell niche that motivated the sale. Andrew affirms Ruslan's self-awareness in choosing to exit cleanly.6:10–8:28 · Andrew pushing back 0/10 Preparation and Listing Strategy on Acquire.com Ruslan shares his proactive approach to asset separation and listing documentation. Andrew reinforces how essential comprehensive upfront preparation is to deal success.8:28–12:46 · Andrew pushing back 0/10 Evaluating Buyer Interest and Selecting the Right Partner Ruslan explains why he preferred an experienced acquirer over higher-bidding novices. Andrew displays clear marketplace expertise, elaborating on pre-due diligence and why veteran buyers close at higher rates.12:46–16:56 · Andrew pushing back 0/10 Due Diligence Hurdles and Asset Transfer Execution Ruslan describes practical bottlenecks during due diligence and asset handover, including codebase vulnerability and a midnight server crash. Andrew empathizes with the operational hiccups.16:56–20:08 · Andrew pushing back 0/10 Key Learnings, Marketplace Liquidity, and Seller Advice Ruslan offers strategic advice on SaaS exits, highlighting the valuation gap between pure recurring revenue and usage-based models. Andrew validates the insights and supports the unique liquidity of Shopify apps.

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

0:00 · Andrew 30.5% · guest 69.5%0:00 · Andrew 30.5% · guest 69.5%3:00 · Andrew 17.4% · guest 82.6%3:00 · Andrew 17.4% · guest 82.6%6:00 · Andrew 39.9% · guest 60.1%6:00 · Andrew 39.9% · guest 60.1%9:00 · Andrew 32.6% · guest 67.4%9:00 · Andrew 32.6% · guest 67.4%12:00 · Andrew 37.4% · guest 62.6%12:00 · Andrew 37.4% · guest 62.6%15:00 · Andrew 19.8% · guest 80.2%15:00 · Andrew 19.8% · guest 80.2%18:00 · Andrew 36.7% · guest 63.3%18:00 · Andrew 36.7% · guest 63.3%21:00 · Andrew 0% · guest 100%21:00 · Andrew 0% · guest 100%
Sharpest disagreement ▶ 0:31 Gentle teasing on brand rename

Ruslan offers mild contrarian critique by telling Andrew that the marketplace's former name, MicroAcquire, had far more character.

 Hardest push from Andrew ▶ 0:48 Host defends brand evolution

Andrew directly responds to Ruslan's comment, defending the brand pivot as necessary to serve larger startups beyond micro-scale.

 Biggest teaching moment ▶ 18:40 Breakdown of valuation discrepancies by revenue model

Ruslan educates sellers on how buyers heavily discount usage-based revenue compared to pure recurring revenue in SaaS acquisitions.

 Andrew holds their own ▶ 9:27 Host outlines why deal certainty beats paper valuation

Andrew demonstrates deep M&A domain expertise, explaining why accepting a lower bid from a seasoned buyer is superior to risking deal collapse with inexperienced buyers.
the scores for every segment, with the reasoning behind each
ChapterTopicAndrew as informed peerGuest teachingGuest disagreementAndrew pushing backWhy
Introducing Ruslan Leteyski and Vanga AI 3211 A friendly opening where Ruslan playfully notes he preferred the company's old name MicroAcquire. Andrew politely clarifies the rationale behind dropping 'micro' before asking about Vanga AI's background and early traction.
Deciding to Sell in a Competitive Market 3200 Ruslan transparently details the fierce competition in the Shopify upsell niche that motivated the sale. Andrew affirms Ruslan's self-awareness in choosing to exit cleanly.
Preparation and Listing Strategy on Acquire.com 4200 Ruslan shares his proactive approach to asset separation and listing documentation. Andrew reinforces how essential comprehensive upfront preparation is to deal success.
Evaluating Buyer Interest and Selecting the Right Partner 6200 Ruslan explains why he preferred an experienced acquirer over higher-bidding novices. Andrew displays clear marketplace expertise, elaborating on pre-due diligence and why veteran buyers close at higher rates.
Due Diligence Hurdles and Asset Transfer Execution 4310 Ruslan describes practical bottlenecks during due diligence and asset handover, including codebase vulnerability and a midnight server crash. Andrew empathizes with the operational hiccups.
Key Learnings, Marketplace Liquidity, and Seller Advice 4400 Ruslan offers strategic advice on SaaS exits, highlighting the valuation gap between pure recurring revenue and usage-based models. Andrew validates the insights and supports the unique liquidity of Shopify apps.

Statements from this episode (9)

Assertion Not checkable as stated
Leteyski: Bootstrapped Shopify app Checkout X scaled to $600k MRR
“I built a Shopify app that became probably the biggest custom checkout on Shopify called Checkout X, which scaled to something around six 100,000 dollars MRR, something like that bootstrap.”
Ruslan Leteyski Jun 13, 2023 ▶ 2:16
Assertion Partly supported
Leteyski: Shopify banned app Checkout X for taking platform revenue
“Then we got banned by Shopify for stealing their revenue.”
Ruslan Leteyski Jun 13, 2023 ▶ 2:30
Opinion
Leteyski: Upselling is the most competitive space in the Shopify App Store
“And ultimately we saw that we were fighting in the most competitive space in the Shopify app store, which is upsetting.”
Ruslan Leteyski Jun 13, 2023 ▶ 4:48
Opinion
Leteyski: Shopify apps were previously illiquid but are now crazy liquid
“Because when I was starting Shopify, absolutely were not liquid at all right now. And they're crazy liquid.”
Ruslan Leteyski Jun 13, 2023 ▶ 5:25
Disclosure
Leteyski: Structuring foreign acquisitions as asset transfers requires careful infrastructure separation
“Because we're a Bulgarian entity. So I was not gonna sell the company. But I needed to figure out how I'm gonna transfer the assets. So even before I started listing, I had to figure out how we can transfer the infrastructure. As I mentioned, we had other proj…”
Ruslan Leteyski Jun 13, 2023 ▶ 6:27
Insight
Gazdecki: Pick experienced buyers over higher offers to ensure deals close
“And I reckon I actually recommend that often for, especially for larger size businesses to Work with an experienced buyer, even if it's at a lower price, because your chances of it closing is so much higher because you can have an inexperienced buyer give you …”
Andrew Gazdecki Jun 13, 2023 ▶ 9:30
Insight
Gazdecki: Pre-due diligence before an LOI dramatically boosts closing odds
“Pre due diligence where you have some calls up front, like you are asked and you respond to some hard questions and that gives you an indication of what it's going to be like working with the buyer before you sign, say a letter of intent. And that's about work…”
Andrew Gazdecki Jun 13, 2023 ▶ 11:57
Insight
Leteyski: In micro-acquisitions, holding account passwords matters more than cap tables
“You realize actually the cap table doesn't matter if the company is like, whoever holds the password is the owner of the company.”
Ruslan Leteyski Jun 13, 2023 ▶ 14:58
Insight
Leteyski: Building and selling Shopify apps after one year is lucrative
“Especially for Shopify apps, where it's like my bread and butter, it's so liquid right now. It's a really good business model to just make Shopify apps and sell them after one year. I think you could make a lot of money bigger.”
Ruslan Leteyski Jun 13, 2023 ▶ 17:51
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