Jun 27, 2023 · 31m · startup-acquisition-stories
Startup Acquisition Stories with Kjael Skaalerud, President of Skaling Ventures
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Host Andrew Gazdecki interviews Kjael Skaalerud, President of Skaling Ventures, exploring micro-private equity strategies, SaaS due diligence scorecards, transparent founder-buyer alignment, post-sale integration, and realistic valuation practices.
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 25.4% of the talking time here. How this is scored →
Andrew as informed peer 4.1 Guest teaching 2.3 Guest disagreement 0.1 Andrew pushing back 0.1
speaking balance: gold is Andrew, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 28:20 Mocking irrational founder valuation expectations
Skaalerud humorously mocks founders who overvalue their startups with inflated emotional bias, urging them to kill that vibe in their soul and look at realistic comps.
Hardest push from Andrew ▶ 26:59 Host reinforces pricing discipline over unrealistic founder compsGazdecki interjects to emphasize that valuation gaps are the primary reason listings fail to sell on his marketplace, validating the point with hard platform experience.
Biggest teaching moment ▶ 14:08 Dismantling traditional PE data room complexitySkaalerud breaks down how bloated legacy data rooms are merely exports of three core systems of record, showing how modern micro-acquisitions bypass paperwork with direct digital integrations.
Andrew holds their own ▶ 27:42 Gazdecki breaks down multi-multiple comp fallacies using SlackGazdecki illustrates his market expertise by dissecting outlier comps like Slack's 26x ARR multiple and warning founders against misapplying enterprise market-leader metrics to small startups.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Andrew as informed peer | Guest teaching | Guest disagreement | Andrew pushing back | Why |
|---|---|---|---|---|---|---|
| Defining Skaling Ventures' SaaS Investment Thesis | 3 | 2 | 0 | 0 | Gazdecki opens with collaborative prompts about Skaalerud's shift from private equity to buying micro-SaaS businesses. Skaalerud walks through his target criteria and scorecard while praising Gazdecki's marketplace. | |
| Quantitative Due Diligence and Retention Metrics | 4 | 3 | 0 | 0 | Gazdecki contributes his observation on buyer-seller goodwill being essential for successful transitions. Skaalerud breaks down his tiered diligence scorecard, cohort retention metrics, and why hypergrowth can paradoxically be punitive for his strategy. | |
| Leveraging Business Flaws and Seller Transparency | 5 | 2 | 0 | 0 | Gazdecki shares insights on why sellers should openly present operational flaws as buyer upside rather than concealing them. Skaalerud strongly agrees and explains how transparent sellers speed up dealmaking. | |
| Due Diligence Preparation and Clean Systems of Record | 3 | 4 | 0 | 0 | Skaalerud educates on modern diligence by contrasting traditional PE data rooms with direct API access to core SaaS systems of record (accounting, CRM/billing, and HR). Gazdecki listens attentively and approves. | |
| Articulating the Value Proposition and Solving Core Problems | 5 | 3 | 0 | 0 | Gazdecki demonstrates his platform experience by explaining how his team rewrites listing headlines to clarify value propositions. Skaalerud outlines a practical 90-day tiered transition model and cap table retention strategy. | |
| Portfolio Strategy and the Value of Building in Public | 7 | 2 | 1 | 1 | Gazdecki demonstrates substantial domain expertise by citing internal marketplace data and comp nuances (such as Slack's acquisition multiple) to reinforce Skaalerud's point about unrealistic founder valuations. | |
| Connecting with Kjael Skaalerud and Concluding Thoughts | 2 | 0 | 0 | 0 | A warm wrap-up where Skaalerud shares his contact details and Substack, followed by mutual appreciation between host and guest. |
Statements from this episode (12)
Skaalerud: Vertical GTM on horizontal SaaS balances TAM and marketing focus
“We were starting to look more closely at horizontal SAS plays and then thinking more about the vertical component from a go to market perspective. To avoid kind of the pitfall of your market to everybody, your market to nobody, but also to avoid kind of the tr…”
Skaling Ventures targets SaaS acquisitions with $10K to $40K MRR
“And then right now we're playing in like the, you know, call it 10 to 40 K MRR. And we have a pretty structured quantitative scorecard that, that addresses some other things. So we fixate a lot of course on net revenue retention logo retention, some stuff like…”
Skaalerud: Skaling Ventures uses debt and fractional teams for transformations
“We used that in our acquisitions and to finance some of the transformation pulling in my team, which is all kind of fractional folks.”
Skaalerud: Acquirers should expect to rewrite 20% to 40% of SaaS code
“Like I think our assumption is that, you know, call it on average, 20 to 40% of the product needs to be enhanced or rewritten in some way. But beyond that, you start to play a game around technical debt and it kind of changes your ability to move fast.”
Skaalerud: Skaling Ventures targets an average 3x ARR multiple for acquisitions
“For instance, an AR multiple, we want to see like on average a three X. So if we see a two X that's rewarded, if we see a five X that's punitive, but it's not a deal breaker.”
Skaalerud: Excessive revenue growth can be a red flag in SaaS acquisitions
“Growth is another one where too much growth is kind of punitive for us because it's like, you know, what are we supposed to do? If the business is already ripping, like that's what we do. So, and then it's also that raises some flags from a seller motive too. …”
Skaalerud: Outlining transformation opportunities speeds up acquisition deals for sellers
“The more you can kind of hint Or foreshadow what a transformation play would look like, and then rationalize why you're not the one to execute it. It'll speed up your ability to transact.”
Skaalerud: Micro-SaaS due diligence replaces manual data rooms with direct software access
“So if you think about traditional OG private equity and it's like, hey, we have a data room and this data room is stuffed full of like spreadsheets that have P and L's and, you know, customer concentration and personnel and salespeople and quotas and headcount…”
Gazdecki: Acquire.com has an in-house team rewriting founder listing headlines
“So when you list on acquire, we'll actually rewrite the headlines. Cause we'll get stuff that's, you know, vertical SAS is revolutionizing this thing. And it is just like, what problem are you solving? And who is it for? That's kind of the main thing. So we'll…”
Skaalerud: $500k-$1M SaaS acquisitions require a 90-day phased founder transition
“And if we're talking kind of, you know, the 500 to a million ARR, which is like, you know, 15 to 25 or whatever, 25 The 45 MRR where there's that level of complexity. You're probably talking about 90 day ideal or three months seller transition, which is 60 hou…”
Skaalerud: Micro-SaaS buyers should retain sellers on the cap table post-sale
“Optimally my view is like, you're selling the business. Let's keep you on the capital stack, like on the cap table. For two, three, four, five, you know, whatever, for like five hours a month, and you're there to advise us on the thing, but ultimately, it's ki…”