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Nov 5, 2024 · 28m · startups-for-the-rest-of-us

Episode 738 | Encouraging Word of Mouth, Educating a Market, and...

Rob Walling · 22m spoken Sean Matthews · 1m spoken
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In this Q&A episode of Startups for the Rest of Us, host Rob Walling delivers tactical advice for scaling SaaS founders, covering enterprise pricing, viral word-of-mouth marketing, market positioning, accelerator partnerships, and employee profit-sharing.

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 87.4% of the talking time here. How this is scored →

Rob as informed peer 8.0 Guest teaching 0.0 Guest disagreement 0.0 Rob pushing back 2.0
05100:0010:0020:001:57–6:38 · Rob as informed peer 8/10 Transitioning to Enterprise Sales and Per-User Pricing Strategy Rob provides comprehensive strategic advice on enterprise SaaS pricing and sales cycles, referencing Jason Cohen's framework. He recommends charging higher prices per user rather than discounting for enterprise accounts.6:39–14:34 · Rob as informed peer 8/10 Strategies for Encouraging Word of Mouth and B2B Virality Rob breaks down the mechanics of word of mouth versus virality, drawing on his 190+ portfolio investments. He shares specific tooling and lifecycle email timing strategies around day 75 to 90.14:35–20:06 · Rob as informed peer 8/10 Market Education Challenges and Opinionated Positioning for Radio Ads Rob applies Eugene Schwartz's five awareness stages and historical examples from Salesforce, HubSpot, and Drip to recommend aggressive, opinionated positioning against legacy radio views.20:06–24:37 · Rob as informed peer 8/10 Partnering with VC Portfolios and Accelerator Ecosystems Rob draws on his direct experience running TinySeed to warn Sean against scraping VC portfolio directories. He redirects the strategy toward official perks pages and sponsorships.24:38–28:24 · Rob as informed peer 8/10 Structuring Sustainable Profit-Sharing Plans for Bootstrapped SaaS Rob references his book and Peldi Guilizzoni's Balsamiq blueprint to outline profit-sharing mechanics, while warning against extreme payout structures that hurt company viability.1:57–6:38 · Guest teaching 0/10 Transitioning to Enterprise Sales and Per-User Pricing Strategy Rob provides comprehensive strategic advice on enterprise SaaS pricing and sales cycles, referencing Jason Cohen's framework. He recommends charging higher prices per user rather than discounting for enterprise accounts.6:39–14:34 · Guest teaching 0/10 Strategies for Encouraging Word of Mouth and B2B Virality Rob breaks down the mechanics of word of mouth versus virality, drawing on his 190+ portfolio investments. He shares specific tooling and lifecycle email timing strategies around day 75 to 90.14:35–20:06 · Guest teaching 0/10 Market Education Challenges and Opinionated Positioning for Radio Ads Rob applies Eugene Schwartz's five awareness stages and historical examples from Salesforce, HubSpot, and Drip to recommend aggressive, opinionated positioning against legacy radio views.20:06–24:37 · Guest teaching 0/10 Partnering with VC Portfolios and Accelerator Ecosystems Rob draws on his direct experience running TinySeed to warn Sean against scraping VC portfolio directories. He redirects the strategy toward official perks pages and sponsorships.24:38–28:24 · Guest teaching 0/10 Structuring Sustainable Profit-Sharing Plans for Bootstrapped SaaS Rob references his book and Peldi Guilizzoni's Balsamiq blueprint to outline profit-sharing mechanics, while warning against extreme payout structures that hurt company viability.1:57–6:38 · Guest disagreement 0/10 Transitioning to Enterprise Sales and Per-User Pricing Strategy Rob provides comprehensive strategic advice on enterprise SaaS pricing and sales cycles, referencing Jason Cohen's framework. He recommends charging higher prices per user rather than discounting for enterprise accounts.6:39–14:34 · Guest disagreement 0/10 Strategies for Encouraging Word of Mouth and B2B Virality Rob breaks down the mechanics of word of mouth versus virality, drawing on his 190+ portfolio investments. He shares specific tooling and lifecycle email timing strategies around day 75 to 90.14:35–20:06 · Guest disagreement 0/10 Market Education Challenges and Opinionated Positioning for Radio Ads Rob applies Eugene Schwartz's five awareness stages and historical examples from Salesforce, HubSpot, and Drip to recommend aggressive, opinionated positioning against legacy radio views.20:06–24:37 · Guest disagreement 0/10 Partnering with VC Portfolios and Accelerator Ecosystems Rob draws on his direct experience running TinySeed to warn Sean against scraping VC portfolio directories. He redirects the strategy toward official perks pages and sponsorships.24:38–28:24 · Guest disagreement 0/10 Structuring Sustainable Profit-Sharing Plans for Bootstrapped SaaS Rob references his book and Peldi Guilizzoni's Balsamiq blueprint to outline profit-sharing mechanics, while warning against extreme payout structures that hurt company viability.1:57–6:38 · Rob pushing back 1/10 Transitioning to Enterprise Sales and Per-User Pricing Strategy Rob provides comprehensive strategic advice on enterprise SaaS pricing and sales cycles, referencing Jason Cohen's framework. He recommends charging higher prices per user rather than discounting for enterprise accounts.6:39–14:34 · Rob pushing back 0/10 Strategies for Encouraging Word of Mouth and B2B Virality Rob breaks down the mechanics of word of mouth versus virality, drawing on his 190+ portfolio investments. He shares specific tooling and lifecycle email timing strategies around day 75 to 90.14:35–20:06 · Rob pushing back 2/10 Market Education Challenges and Opinionated Positioning for Radio Ads Rob applies Eugene Schwartz's five awareness stages and historical examples from Salesforce, HubSpot, and Drip to recommend aggressive, opinionated positioning against legacy radio views.20:06–24:37 · Rob pushing back 4/10 Partnering with VC Portfolios and Accelerator Ecosystems Rob draws on his direct experience running TinySeed to warn Sean against scraping VC portfolio directories. He redirects the strategy toward official perks pages and sponsorships.24:38–28:24 · Rob pushing back 3/10 Structuring Sustainable Profit-Sharing Plans for Bootstrapped SaaS Rob references his book and Peldi Guilizzoni's Balsamiq blueprint to outline profit-sharing mechanics, while warning against extreme payout structures that hurt company viability.

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

0:00 · Rob 99.2% · guest 0.8%0:00 · Rob 99.2% · guest 0.8%3:00 · Rob 100% · guest 0%3:00 · Rob 100% · guest 0%6:00 · Rob 100% · guest 0%6:00 · Rob 100% · guest 0%9:00 · Rob 100% · guest 0%9:00 · Rob 100% · guest 0%12:00 · Rob 93.8% · guest 6.2%12:00 · Rob 93.8% · guest 6.2%15:00 · Rob 86.1% · guest 13.9%15:00 · Rob 86.1% · guest 13.9%18:00 · Rob 74.2% · guest 25.8%18:00 · Rob 74.2% · guest 25.8%21:00 · Rob 65.5% · guest 34.5%21:00 · Rob 65.5% · guest 34.5%24:00 · Rob 61.6% · guest 38.4%24:00 · Rob 61.6% · guest 38.4%27:00 · Rob 100% · guest 0%27:00 · Rob 100% · guest 0%
Sharpest disagreement ▶ 21:40 Sean Matthews anticipates pushback from VCs

Sean acknowledges that cold-pitching VCs might be rejected immediately because investment funds get bombarded with sales pitches constantly.

 Hardest push from Rob ▶ 22:05 Rob shuts down portfolio scraping

Rob bluntly tells the listener that scraping portfolio lists and cold-emailing founders triggers backlash and damages founder reputations in private communities.

 Biggest teaching moment ▶ 15:00 Flores presents the paradox of modern radio ads

Flores explains how online marketing channels struggle to sell radio ads due to deeply entrenched traditional biases among prospective buyers.

 Rob holds their own ▶ 17:30 Rob demonstrates positioning masterclass

Rob illustrates how to attack entrenched competitor perceptions by recounting Drip's anti-competitor positioning campaign and Eugene Schwartz's awareness framework.
the scores for every segment, with the reasoning behind each
ChapterTopicRob as informed peerGuest teachingGuest disagreementRob pushing backWhy
Transitioning to Enterprise Sales and Per-User Pricing Strategy 8001 Rob provides comprehensive strategic advice on enterprise SaaS pricing and sales cycles, referencing Jason Cohen's framework. He recommends charging higher prices per user rather than discounting for enterprise accounts.
Strategies for Encouraging Word of Mouth and B2B Virality 8000 Rob breaks down the mechanics of word of mouth versus virality, drawing on his 190+ portfolio investments. He shares specific tooling and lifecycle email timing strategies around day 75 to 90.
Market Education Challenges and Opinionated Positioning for Radio Ads 8002 Rob applies Eugene Schwartz's five awareness stages and historical examples from Salesforce, HubSpot, and Drip to recommend aggressive, opinionated positioning against legacy radio views.
Partnering with VC Portfolios and Accelerator Ecosystems 8004 Rob draws on his direct experience running TinySeed to warn Sean against scraping VC portfolio directories. He redirects the strategy toward official perks pages and sponsorships.
Structuring Sustainable Profit-Sharing Plans for Bootstrapped SaaS 8003 Rob references his book and Peldi Guilizzoni's Balsamiq blueprint to outline profit-sharing mechanics, while warning against extreme payout structures that hurt company viability.

Statements from this episode (8)

Insight
Enterprises should pay higher per-user prices, not lower, due to overhead
“Enterprise would pay a higher price per user, not a lower price. And that's because they need things like custom terms of service. They need to be able to redline everything. They need to be able to have invoices and POs, which are probably already doing at 75…”
Rob Walling Nov 5, 2024 ▶ 5:44
Insight
Walling: B2B SaaS cannot reliably control or manufacture word-of-mouth marketing
“Trying to encourage word of mouth marketing is something I have never seen B to B SaaS do well. I've never seen a silver bullet is more of what I should say. There are ways to encourage it, and I'm going to run through a few of those here, but there's no way t…”
Rob Walling Nov 5, 2024 ▶ 7:19
Insight
Walling: Referral incentive programs are far less effective for B2B than B2C
“I know people who have refer a friend or affiliate programs and refer a friend, you get a month free, they get a month free. That's fine. That works well with B to C. I find that it works perhaps less well with B to B. I'm not saying you shouldn't do it, but a…”
Rob Walling Nov 5, 2024 ▶ 12:09
Assertion Not checkable as stated
HubSpot spent up to eight figures defining 'inbound marketing'
“I talked to Dharmesh at one point. He said it took millions of dollars, it might even have been eight figures, and several years To kind of define that term, and it's expensive and it takes a long time.”
Rob Walling Nov 5, 2024 ▶ 18:16
Insight
Walling: Never scrape VC or accelerator portfolio pages for cold outreach
“One approach that you should not take is to scrape the portfolio companies from a website and cold outreach them one at a time. Because it really pisses people off.”
Rob Walling Nov 5, 2024 ▶ 22:06
Insight
Walling: Accelerator perks pages require 25-45% discounts or free first years
“The thing there is it has to be significant. It's not a 10% discount. That doesn't get you on perks pages. You know, you're talking 25, 35, 45% discount, like something noticeable, or like free for the first year.”
Rob Walling Nov 5, 2024 ▶ 23:48
Insight
Walling: Structure profit-sharing as a pooled percentage rather than individual allocations
“Consider structuring profit sharing as a pool rather than a committed percentage to an individual. For example, instead of telling early employees they get one, two, or three percent of profits, have all key employees share in a 10 or 15% profit sharing pool.”
Rob Walling Nov 5, 2024 ▶ 26:17
Opinion
Walling: Distributing over 50% of profits to employees threatens company viability
“I believe there was someone who was giving away more than 50% of their profits to their employees, and that, it makes your business, ah, I'll say almost inviolable. It's just, if you ever go to sell, like, it's just not a great way to structure profit sharing.…”
Rob Walling Nov 5, 2024 ▶ 27:54
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