Here's why I'm going ALL IN on paid ads for RB2B and a FULL BREAKDOWN of our funnels and campaign strategy across LinkedIn, Meta and YouTube.

The Origin

In 2020, my wife Helen and I did a weekly 60 second Facebook ad for GetEmails (now Retention.com). Anybody on LinkedIn remember seeing them?

My basic idea was:

1. Two trustworthy-looking people answering
2. The sales questions everybody asked in a
3. Funny, light-hearted way, using
4. Dumb props w/ different backgrounds every time

The campaign took on a life of its own… They ended up being hilarious, inflammatory, and created an EPIC amount of awareness in our TAM… And it ended up being a major reason GetEmails got off the ground.

———

Fast forward to 2024… Organic LinkedIn was the weapon of choice because of the author-audience-platform fit I enjoy with our base of prospects. I never even thought of going outside of LinkedIn, until I saw what Ryan Allis was helping people put together at SaaSRise … It's basically cold email + audience match and retargeting ads across platforms.

I also saw how well Instantly has been doing with the strategy… and I wanted to see if we could get something similar going.

The Catalyst

So...I called in Understory, who are the kings of ALLBOUND. I told them what I was trying to do, they said "no problem, all we need is content".

They dropped what felt like a HUGE ask:

1. 5 videos talking about something about RB2B
2. 3 motion-graphic workflow-style videos showing the software
3. 3 testimonials of customers talking about how they use it and ROI

After recording these videos, something clicked. I remembered what it felt like to record those Facebook ads almost 5 years ago.

And the strategy I used would probably still be relevant:

• People ask the same six sales questions
• Make selfie videos about them
• Run them as web retargeting ads

My wife's pretty face would not be part of them, but I think that's now offset by the fact that I was totally unknown in 2020 and lots of people now recognize me from my video first personal brand. We'll see...

The Bottom Line

Sometimes the best strategies are the ones that worked before. Those Facebook ads from 2020 proved that authentic, direct video content cuts through the noise. Now with RB2B's growing recognition and a multi-platform approach, we're betting big that the same playbook will work even better.

The 20 videos are live, the funnels are built, and we're about to find out if lightning strikes twice.

Want the full breakdown of our campaign strategies and funnels across LinkedIn, Meta, and YouTube retargeting? Click here to connect with me on LinkedIn.

Here are five reasons why I don’t measure any marketing activity I spend time on.

The Most Important Things Are Unmeasurable

The two things that come to mind when I say this are “brand” and “demand creation.”

I can’t measure the direct effect that anything I spend 80% of my time on has on RB2B. I have no idea how many signups came from this post, and I don’t know what the three podcasts I did last week produced.

Yet, I know it’s working better than anything I’ve done before. If I were optimizing for things I could see with my own eyes (beyond MRR), my days would look totally different.

You Can Only Measure Demand Capture

The least important parts of business are what you can actually measure.

You can only measure demand CAPTURE—when someone clicks on an ad, books a demo, hits your site from Google, or responds to a cold email or LinkedIn DM.

Measurement Leads To Misguided Optimization

How do we respond to only being able to measure demand capture? With more paid ads, SEO, cold email, and LinkedIn messages. These activities are only CAPTURING demand, not creating it.

Executive teams don’t have the patience to scale demand creation. Six months in, the CEO asks how many leads we got from the podcast or organic social. When the response is “I don’t know,” the budget goes to paid search.

Attribution Platforms Are Often Wrong

This bothers me more than anything else. So many of our customers have already made up their minds to buy before they were ever shown a retargeting ad.

But, LinkedIn still claims the retargeting conversion. The reality is that the buyer came from listening to me on someone’s podcast or from reading my posts.

Am I supposed to believe that our ROAS is positive? I’m really not sure.

Spreadsheets Don't Reflect Reality

We’ve all seen the model: “If we hire X people in Y department, we’ll grow by Z.”

I've made this rookie mistake, and I think most CEOs are right there with me.

I believe it never works because we don’t appreciate how important the unmeasurable, TRUE components of business growth are. Brand and demand creation activities don’t fit anywhere on that spreadsheet.

Human Connection

It’s 2025. As outbound continues to die, the unmeasurable becomes ever more important. The quickest way to grow a SaaS business is by building a brand. The best way to scale a brand is by building a personal (not company) profile.

Demand today is actually created through human-to-human connection, and social media platforms facilitate this connection at a massive scale.

I’m creating human-to-human connection by:

1. Pouring my thoughts (and heart) out on LinkedIn
2. Responding to every comment someone leaves
3. Hosting a weekly LIVE and interactive event

I can’t measure what any of it is doing to our business. Except for the most important measure of all…

ARR… up-and-to-the-right!

Conclusion

Traditional marketing attribution often misses the mark.

Here are the key takeaways:

• Focus on the Unmeasurable: The most critical growth drivers, like brand building and demand creation, cannot be tracked with standard attribution tools.
• Don't Mistake Capture for Creation: Measuring ad clicks and demo requests (demand capture) is easy, but it ignores the activities that created the demand in the first place.
• Avoid Misguided Optimization: Over-relying on measurable data leads to pouring budget into scalable but less effective channels, like paid ads, at the expense of brand building.
• Embrace Human Connection: True demand is built through authentic, human-to-human interaction on platforms like social media.
• The Ultimate Metric is Revenue: The only metric that truly matters is bottom-line growth (ARR), not the flawed data in an attribution report.

Instead of getting lost in spreadsheets and vanity metrics, the focus should be on activities that genuinely drive growth, even if they can't be measured precisely.

Thanks for reading! You can follow me on LinkedIn, X or Patron View for more updates.

Here's my stats.

The Numbers

My AI clone has had 1,683 conversations in 22 days. That's roughly 76 conversations per day, working around the clock while I do more important things.

Here's the breakdown:

• 304 demos delivered without me lifting a finger
• 98 SOC2 docs sent to prospects who needed them
• 16 custom pricing quotes delivered with precision

Quality Check

85% great, 10% meh, 5% wrong.

The performance breakdown shows my AI clone is hitting home runs most of the time, with only minor hiccups that are quickly improving.

Conclusion

The numbers speak for themselves - 1,683 conversations, hundreds of demos, and consistent performance that never sleeps.

What does this make me? A VIBE SELLER.

Follow me on LinkedIn, X or Patron View for more content like this.

After working with hundreds of entrepreneurs and making countless mistakes myself, I've identified a clear pattern of destructive behaviors that plague nearly every new founder.

Here are the 7 biggest mistakes I see nearly EVERY founder make (myself included).

Overspending

You spend too much money on things you don't really need.

People love getting offices, hiring salespeople, getting VA's, expensive video equipment, software, and even setting up an entity pre-revenue. In 2013, I bought a VOIP phone system a year before we had a customer!

Cash will be EXTREMELY tight at some point, even if it's not now. Remember that.

Early Hiring

Hiring people before $1M ARR.

This is a hot take. I think there should be a technical co-founder building and a business co-founder doing sales, marketing, and support until $1M ARR - just like Klaviyo did.

If you have that discipline, you will be profitable, control your destiny, and emerge with product-market fit.

Ideas Guy

Thinking you are an "ideas guy" and can find an operator.

I spit out my drink when I hear this. Just like when I hear someone talking about "stealth mode". Thinking someone will do the hard work for you at this nearly impossible stage is delusional.

Once you get to $10M ARR with under 10 people, you earned it, but until then, no way.

Scaling Prematurely

Not "doing things that don't scale" under $1M ARR.

First-time founders don't understand how manual getting to $1-$3M ARR is. It's face-to-face conversations, however you can get them, taking the feedback, and improving product as quickly as possible.

Nothing will work until the product is great, so all that "growth hacking" will be a waste of time and money.

Funding Delusion

Thinking seed funding means you have a good business.

If you were able to raise money for your idea pre-revenue, it means nothing more than you could sell a vision to investors. The hard part is making a business out of it.

Keep that in mind and avoid funding at all costs. You'll thank me later.

Social Neglect

Not posting on organic social media starting TODAY.

This one took me a decade to realize, and a year after I started to master. Nothing is more powerful in today's world than being able to create great organic social media content that your prospects have demand for independent of what you're selling.

If you start today, you'll get zero engagement, followers, or leads, but that's not the point… You're one day closer to finding your voice.

Short Timeline

Thinking you'll be in and out in 3-5 years.

Founders should have a decades long time horizon when they start. People wildly overestimate what they can accomplish in a year, but wildly underestimate what they can accomplish over a decade.

Conclusion

Being a first-time founder is hard. Literally everything is working against you. If we knew how hard it was, most would never start.

To recap, here are the 7 deadly mistakes to avoid:

• Overspending - Don't buy things you don't really need
• Early Hiring - Stay lean until $1M ARR
• Ideas Guy - Don't expect others to do the hard work
• Scaling Prematurely - Do things that don't scale first
• Funding Delusion - Raising money ≠ having a good business
• Social Neglect - Start building your organic presence today
• Short Timeline - Think decades, not years

But here's the good news...

As Alex Hormozi so elegantly put it: Every successful person started with 0 revenue, 0 subscribers, 0 customers, 0 fans. And the only difference between them and everyone else is they actually start.

But that's not REALLY the secret. The successful ones not only start… They keep building.

Thanks for reading. Follow me onLinkedIn, X orPatron View for more.

The path from $1M to $10M ARR is where many promising startups hit an invisible wall.

Mid-Stage Growth Challenges

In the past 6 months, I've spoken to over 50 founders doing $1M-$10M ARR. 99% of them feel STUCK.

The transition from early-stage scrappiness to scale-ready operations isn't just about doing more of what got you here—it requires fundamental shifts in how you think about your product, customers, and business model.

Here are the 6 biggest mistakes they're making that prevent them from unlocking growth to $10M ARR:

Same but Better

It's easy to get early traction when you're a little bit better than the incumbent. To reach scale, you need to be 10x better than what people are already using to get them to switch.

Incremental improvements might win you early adopters, but they won't drive the massive customer acquisition needed for serious scale.

The switching costs—both financial and operational—are too high for most customers to move for marginal gains.

Messaging Isn't Clear Enough

Crystal-clear messaging helps everything. Unclear messaging hurts everything. A decent product with subpar messaging can get to a few million ARR.

You have to tighten it up to get to $10M.

When your messaging is muddy, every aspect of your business suffers. Sales cycles lengthen, conversion rates drop, and even your best customers struggle to refer you effectively.

The companies that break through to $10M+ have messaging so clear that prospects immediately understand the value proposition.

Don't Know Ideal Customer

Taking money from anyone and everyone is often what you have to do in the beginning. Honing in on an ideal customer and building for them will often get you unstuck.

The "spray and pray" approach that worked in the early days becomes a liability at scale.

Without a clear ideal customer profile, your product roadmap becomes scattered, your marketing becomes ineffective, and your sales team wastes time on prospects who will never become great customers.

Understanding Unit Economics

If you don't know what's working and what's not, you don't know what to scale and what to pull back on.

Many startups do everything in the beginning and stall out because they have no idea what was is actually working and what isn't.

The experimental phase of early-stage growth often creates a patchwork of initiatives without clear attribution.

When you can't identify which channels, campaigns, or customer segments are actually driving profitable growth, scaling becomes a guessing game rather than a data-driven process.

No Word-of-Mouth

If you have word-of-mouth, everything you do will work. If you don't have word-of-mouth, nothing you do will work.

Some startups capture initial excitement but fail to deliver on promises made and lose this critical tailwind.

Word-of-mouth is the ultimate growth multiplier. It reduces customer acquisition costs, shortens sales cycles, and brings in higher-quality customers.

Without it, every customer feels like you're pushing a boulder up a hill.

Churn is Abysmal

RB2B is guilty as charged. We're working every day on a total reinvention, and if you also have abysmal churn at mid-single-digit ARR, you should tirelessly improve your product too.

High churn at this stage isn't just a retention problem—it's a fundamental product-market fit issue that needs immediate attention.

No amount of marketing or sales optimization can overcome a leaky bucket.

The Path Forward

Startups are hard. My life for the last 12 years has been getting stuck, then unstuck again.

In fact, I'm stuck right now!

The good news is that no matter how stuck you feel:

• There are thousands of founders who are stuck right there with you.
• No matter how stuck you are, you can get unstuck—it's in your hands.

I'm here to tell you: don't get defeated. The rewards for blowing past $10M ARR are unimaginable.

Remember, feeling stuck is part of the process. The key is using that feeling as a signal to step back, reassess, and make the bold moves that will unlock your next phase of growth.

The $10M milestone isn't just a revenue target—it's proof that you've built something truly scalable and valuable.

Keep building.

This conversation reveals important perspectives on bootstrapping versus taking VC funding.

Transcript

Sam Parr: My friend sold his startup for $1b and only cleared $3m (pre-tax).

Me: What?!? How???

Sam: He raised $400m of VC from Seed to Series E and had 4 co-founders. 1.2% total founder ownership after employee options.

Me: And he didn't take any secondary?

Sam: Nothing meaningful. He didn't have the leverage.

Me: That sucks.

Sam: Tell me about it.

Me: You talk to TONS of wealthy entrepreneurs about how they did it. How do you avoid having this happen to you?

Sam: The problem with VC is that you are signing up to ultimately own 10% or less of something that has a 70% or greater chance of failing. If you just don't raise, or raise as little as possible, the odds that you will have something smaller, own most or all of it, that has a much higher chance of succeeding... and be wealthy... are much higher.

Me: Have you ever taken VC?

Sam: Nobody would invest in The Hustle, which felt horrible at the time, but ended up being incredible for me personally. I sold it for more than what you see on the internet (which is high 20mm's FWIW), bought the S&P index with the money (which is up 45% since I sold), and didn't have to give anything to any investors. So I look like a genius compared to my $3m friend.

Me: Would you take VC now?

Sam: Now I would use VC money, but I'm post liquidity. I would want to really try for something big, and it wouldn't really crush me if I wasted a decade on something that failed. Pre-liquidity it would have.

Me: What does "post-liquidity" mean?

Sam: I asked a bunch of wealthy friends how much money they spent. One guy who I really respected said $600k. I divided that by 3%, and it gave me $20m. After The Hustle, I cleared $20m and then some. So, that, for me, is "post-liquidity".

Me: So you think no VC until post-liquidity?

Sam: Some businesses absolutely require VC. I invested in a robotics company that used a TON of capital and made the founder a billionaire. But, in general, if you want to get wealthy, use little or no investor money.

Me: Fair. One more thing.

Sam: What's that?

Me: Asking for a friend... How does someone who bootstrapped $25m ARR and is going to do $14m in profit this year get on My First Million?

Sam (smiling): Email me ... and come up with the angle!

Conclusion

This conversation highlights a crucial insight for entrepreneurs: while venture capital can fuel rapid growth, it often dramatically dilutes founder ownership.

For many founders, bootstrapping may offer a more reliable path to personal wealth, with Sam's experience selling The Hustle serving as a compelling example of maintaining ownership while achieving significant financial success.

She then spent 3 hours manually building a prospect list, and ABM'd 100 highly personalized emails to female CMOs… and we got ZERO responses back.

WHAT?!?!? She was devastated.

What CMO wouldn't want to go to see the Taylor Swift Era's concert.

In a box, with free champagne, a custom Taylor Swift cocktail, and some free Swiftie Eras swag?

It didn't make any sense.

The LinkedIn Pivot

But then she reached out to this same group of "Dream 100" CEO's on LinkedIn.

And she got a VERY different response.

All of a sudden, she was getting "YES" from CMO's of massive ecommerce brands.

She asked them why they didn't respond to the email.

It turns out ALL of them received the email, and they all read it.

But they didn't write back because the event sounded too good to be true!

The show was a hit, and we're now in conversations with a handful of CMOs that we wouldn't have even DREAMED of pursuing 12 months ago.

Conclusion

What's the lesson here? I think it's two parts.

1. Create events that are so good that people don't believe they're real, because in 2025, that's what it takes to break through the noise.
2. Make sure they know you're a human and that you're for real.

LinkedIn is the best place for this.

Who's in for the next Taylor Swift box with the Retention.com team?

Follow me on LinkedIn for more content like this!

I'm about to show you why using the “Swag-Led Outbound Approach” on potential customers isn't just a nice-to-have—it's the next big GTM revolution.

In November, I spent $7,500 on cold emails, $10,000 on SEO, $33,000 on LinkedIn ads, and $20,000 on high-quality video.

Then I turned it all off. Why? Because I'm going to invest $25,000/mo in my newest GTM motion.

I'm calling it Swag-Led Outbound (SLO)

Here's why I'm betting $25K/month on it.

Swag-Led Outbound Playbook

Here’s my 8-step plan:

Step 1: Create the Swag

• Get NoBoringDesign to create the dopest swag ever.

Step 2: Generate Buzz

• Post about it, do a giveaway, and make it go viral.

Step 3: Engage the Community

• Send swag to people who say they’ll post about it.

Step 4: Reward Demos

• Give a hoodie to every single person that takes a demo.

Step 5: Reward Founders

• Send a full swag box to everyone who joins the $10M ARR Club (my private community for startup founders—DM me if you want to join).

Step 6: Event Outreach

• Walk around industry events and hand out cards with QR codes linking to the store, offering coupon codes for t-shirts or hoodies.

Step 7: Targeted Outreach

• Outbound people who we want to look at RB2B with a swag box.

Step 8: Reward UGC Creators

• Send all of our UGC creators a swag box.

Conclusion

I want to invest an irresponsible amount of $$$ getting B2B people our SWAG.

I think it's going to lead to breakout growth in 2025. It could very well be the future of go-to-market.

And that's why I'm calling it... “Swag-Led Outbound”.

Follow me on LinkedIn for more content like this!

Two years later, the money's gone, and his ARR is flat.

If you asked him what his biggest mistake was, what do you think he would say?

He would tell you… hiring salespeople.

To be clear, it wasn't JUST hiring salespeople, it was HOW he hired them.

Private Equity Warning

Another founder buddy of mine recently did a Private Equity (PE) round.

His investors were pushing him to grow his team of reps from 5 to 20.

Fortunately, my PE backed friend talked to my CEO friend first.

The Conversation

PE backed friend: We just raised $25m, and they want us to hire a bunch of salespeople.

CEO: Of course, they do. But don't do it yet. That pressure is EXACTLY what smoked me, wasted 2 years and $40m, and very likely shaved 10 years off my life.

PE backed friend: Ok... well... what do I do?

CEO: Are all of your reps at 100%?

Pe backed friend: Not really. One might be, the rest aren't.

CEO: Do not hire ONE MORE REP until ALL of your reps are at 100% capacity. If you build a machine that has slack in it already, you will experience all sorts of cultural and motivational problems. The same amount of demos your marketing machine is creating and reps are capturing will go to even MORE people. Your team will miss numbers week in and week out. You will attempt to solve that problem by demanding reps you hired to be AE's do more and more outbound. That will not work. Your sales leader will probably either quit or be fired, because you'll have the exact same productivity on 4x the team size.

PE backed friend: That's terrifying. Especially now that we're PE backed.

CEO: Tell me about it.

Pe backed friend: What do I do instead?

CEO: Before you hire a SINGLE REP, make sure all of your reps are at 100% capacity. Make sure your marketing machine can actually produce more pipeline. If and when you can actually flood your reps with activity and the entire team is at 100%.

PE backed friend: Then I hire reps?

CEO: NO!!!! Absolutely not. You work on raising the 100% higher. Can you create AI agents that save account research and follow-up time? Can you hire sales assistants to do some of the unavoidable repetitive work? ANYTHING to make your already 100% capacity reps more productive. Then, and only then, do you start slowly adding reps to the team.

PE backed friend: I am so glad I spoke to you before I did anything.

CEO: Me too.

Conclusion

Institutional capital still wants to push founders into rapidly hiring reps to accelerate growth.

While that sometimes works, it's VERY easy to do it the wrong way.

The Right Way to Scale:

1. Make sure your marketing machine can grow
2. Get all your reps to 100% capacity
3. Raise that capacity as much as possible
4. Slowly add reps to THAT machine

Build your team that way and you can't lose.

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This story is about one of those moments that validated my entire entrepreneurial journey.

A CEO friend of mine just shut down his startup after 12 years.

He raised over $30m in VC, and the co-founders' families put in $2m.

In 2017, he tried to hire me, saying they'd “soon be worth $1B.”

Here’s the full story.

Conversation That Changed Everything

This was our conversation:

CEO: You're not ambitious enough.

Me: What???? Why do you say that?

CEO: It's been 5 years, man. You're wasting your life on your tiny startup. It's not going anywhere.

Me: Yeah, but it's MY tiny startup.

CEO: We'll be worth a billion soon. A small part of my startup will be worth so much more than your large stake of yours... And you'll have a bigger impact working for us.

Me: I have two main objections. First, paradise to me is a mid-20's ARR SaaS with under 40 people. I don't know how I'm going to get there, but that's what I'm going for. Second, even if my startup is worth less, and it's less impactful, it's MY startup, which your startup is not. You work for the VCs. I'd rather spend my time working on my own thing, even if I stay stuck here.

CEO: You're too talented to be thinking so small.

The Outcome

You already know how the story ends.

I now have my mid-20 ARR startup with 40 employees.

Here's the craziest thing.

We generated $1m in profit the same month he closed his doors.

Believe me, my friend no longer thinks I'm “not ambitious enough.”

Lessons for Bootstrappers

Here are my 4 key lessons:

1. The world is really hard on you when you're small. Stay strong.
2. If you're small but profitable, you can stay in the game.
3. The skills and effort you're compounding are VERY valuable.
4. If you build skills and stay in the game long enough, the odds that you will get lucky and hit it big skyrocket.

Conclusion

Don't let people tell you that you're wasting your life.

Massive success is inside all of you.

It just takes LOTS of time, and usually a little luck.

Keep building.

Follow me on LinkedIn for more content and tips like this.

It's not complicated, but it's been a game-changer for building our team.

Type of People I Look For

I look for people who would make great founders themselves, but who aren't ready to take that leap yet.

Maybe they've got family commitments or they're just more risk-averse.

That's fine - it actually makes them perfect hires.

How to Keep People Happy

The trick is how you manage them.

These people need to truly own their part of the business. I mean complete ownership, like it's their own mini-startup within the company.

Here's how you can do that:

1. Don't micromanage them
2. Don't try to control their decisions
3. Don't restrict their creativity

If you start getting controlling, they'll leave. And they should - that's not what they signed up for.

Why This Matters

When you give people this kind of freedom, it creates an incredible culture.

It's really that simple - find great people who could be founders, give them space to build, and watch what happens.

This conversation captures Oren's fascinating perspective on how AI technology is set to transform business operations and customer service delivery.

AI & Customer Support

Here’s what Oren said to me:

“I think what's interesting is how AI is going to affect this whole market of conversational e-commerce. There's probably millions of customer support people handling simple questions in the Philippines, India, and Dominican Republic.”

Wow. I’ve never thought about it like that.

He continued:

“Wherever we implement OpenAI with our unique models and put some of our tech in it, I have to tell you: 40-50% of the time, it brings out a perfect answer. It's still not good enough, and we believe in the human connection.”

That’s wild! And it’s only going to get better.

Oren agreed:

“Five years from now, I don't think you're going to need human support. I think there's going to be so much turmoil in the entire BPO business and in the technologies that just provide a platform for support, especially support if you have a problem with your device.”

Looking Ahead

Oren's perspective highlights a significant shift in customer service operations.

While current AI solutions achieve 40-50% accuracy in handling customer inquiries, rapid advancements suggest a future where AI could manage most standard support interactions.

This transformation will likely reshape the global BPO industry and redefine how businesses approach customer service delivery.

Follow me on LinkedIn for more content like this!

As a sales consultant, he believes he only has 3-4 years left in the game.

Here's why, and what the future looks like.

Three Major Shifts

Plummeting Response Rates

I often hear people say, "You're an idiot for claiming the Predictable Revenue model is dead - it never should have worked for your $25k ACV anyway."

But here's the reality:

Response rates have dropped 50% in just the last 18 months. Let's do the math.

That pushes the minimum deal size to $50k. In another 18 months? Another 50% drop, pushing it to $100k. And 18 months after that? We're looking at a $200k floor for outbound sales to make sense.

Think about it - how many sales reps today are selling products over $200k? Almost none.

Traditional Channels Are Dying

Scott and I never use our phones anymore - they're permanently on silent.

We only read emails from people we know. But here's the real kicker: Scott's teenagers (14 and 16) don't even use email or text.

They communicate exclusively through Snapchat and Instagram DMs. What we're seeing now isn't just cracks in the foundation - we're heading for a complete collapse.

Buyers Are Avoiding Salespeople

Scott recently bought a $1.1m investment property in Chicago without talking to a single person.

Amazon is dominating because people can get anything they want with a few button clicks from their couch. The old guard on LinkedIn (and I'm 43) insists people want human interaction. I think they're wrong.

Future of B2B Sales

The shift isn't a question of if - it's when.

Here's what's coming:

1. Sales teams will function more like editorial teams
2. They'll focus on creating authentic content that meets buyers on their preferred platforms
3. Teams will be smaller but have much broader reach
4. They'll scale human-to-human connection through content

New Sales Model

One "builder" will run the machine that:

• Listens to signals from the content engine
• Nudges prospects through the funnel
• Captures them when they're ready to buy

Sales cycles will shrink dramatically because awareness, education, and nurturing will be almost completely automated.

New Sales Environment

These teams will be:

• Lean and hyper-efficient
• Fun to work for
• Staffed by "artist" reps who create content
• Focused on talking to ready-to-buy prospects only

Survival

Tomorrow's sales leaders need one of two skills:

1. Building organic social media audiences
2. Engineering scalable signal-based selling machines

If you can't do either, you're out of the game.

Conclusion

The transformation of B2B sales isn't coming - it's already here.

The traditional outbound model is falling apart faster than most people realize, and the future belongs to those who can adapt to this new content-driven, signal-based approach.

Retention.com works 10 to 15 times better than the next best option out there.

What we achieved with this customer’s implementation showcases exactly why our solution is transforming email marketing.

We doubled their list size in just 40 days while improving deliverability and growing product views by 25%.

Here's how this implementation transformed Bruce Bolt’s email marketing strategy.

Initial Challenge

The original welcome series had very high positive engagement, but also had high negative engagement.

This typically isn't a problem because it's such a small percentage of the overall email flow going out.

But if you're sending a welcome series, it just hurts to see those numbers.

The Solution

When new contacts come through your website, instead of placing them in a standalone welcome series, we held them in a segment and included them in a larger newsletter.

This approach minimizes the impact of any negative engagement, as they make up just 1% of the total recipients, diluting their effect within the broader send.

The Numbers

Here are some numbers before and after showing you the difference.

Before Implementation

We were putting 500 to 1000 contacts per day into Klaviyo's welcome series.

The complaint rate was 0.48 (it needs to be below 0.1, ideally 0.05), and the unsub rate was 3.56%—which in a flow looks like garbage.

Previous Newsletter Performance

Their old newsletter showed incredibly low spam rates with a size of 136K and unsubs at 0.2%. These metrics set our baseline for active on-site engagement and page views.

After Implementation

With the Bruce Bolt implementation, email list growth was tremendous in just the first 40 days.

The spam rate and unsubscribe rate didn't increase in any meaningful way that caused concern.

Most importantly, product views grew from 2.3k to 4k — that's almost 100% growth with not as much list size growth.

Conclusion

The Bruce Bolt implementation highlights how Retention.com can revolutionize email marketing strategies.

By doubling their email list in just 40 days, we not only improved deliverability but also boosted product views by nearly 100%—all while maintaining strong engagement metrics and minimizing the impact of negative interactions.

This approach proves that growing your list doesn’t have to come at the cost of performance.

For more case studies like this, follow me on LinkedIn!

Check out retention.com if you'd like to learn more about our services.

Now I'm working on doing it a third time with rb2b.com.

Here's what I've learned about bootstrapping a successful startup.

Advice for Bootstrappers

Here are 6 of my best advice for bootstrappers:

Be Extremely Frugal

I made so many unnecessary spending mistakes in my early days.

I bought a phone system I didn't need. I rented an office that was completely unnecessary. I lived in an expensive Manhattan apartment. I even bought two expensive cameras for content that I only used once.

Your money is your lifeline - be incredibly careful with it. Things will get extremely tight before you succeed.

Focus on Product-Market Fit

When you achieve true product-market fit, everything flows naturally and feels easy.

Without it, everything's a constant struggle. I've experienced both sides.

Until your product grows through word-of-mouth, focus entirely on making it better.

Master Marketing Skills

Once your product is solid, the best way to grow a SaaS today is through high-velocity inbound marketing.

Learn everything: offers, funnels, conversion, paid ads, organic social, differentiation, channels, content, and pricing.

Having deep marketing knowledge yourself is much better than relying on others for core business decisions.

Be Strategic with Hiring and Firing

Don't hire your first employee until you're completely overwhelmed. Wait to hire the next one until everyone's struggling again. It's hard to fire people at first, but experienced founders know to cut ties the moment something isn't working. As someone told me, "I never regretted letting someone go, I've just regretted not doing it sooner."

Start Small

While big ambitions are great, larger ideas are usually more complex and harder to execute.

I started small, and each of my ventures has grown significantly larger than the last.

Choose Great People

Our odds of creating huge companies are small.

We might create an average company, or more likely, fail entirely.

Any of these outcomes are manageable if you're working with great people.

Even massive success feels hollow if you're surrounded by the wrong team.

Conclusion

These lessons come directly from my experience building multiple successful businesses.

I'm using them right now as I build my third venture, and they're still proving true.

Here's what I've realized: 99% of startups are focused on the wrong thing.

They're obsessed with predictable revenue, but I believe the next wave of billion-dollar unicorns will prioritize sales velocity instead.

8 Reasons

Here are 8 reason velocity will define the future:

1. Revenue was never actually predictable. Everyone got it wrong - we all underestimated our numbers in 2021-2022 and overestimated them in 2023. Meanwhile, we kept making staffing decisions based on those year-end growth targets.
2. The way prospects research has changed completely. The best go-to-market strategies now focus on reaching prospects early and often with helpful content during their research phase. When you make it easy for non-ready buyers to access your content, you win more deals later.
3. Outbound channels are totally burned out. Response rates have dropped by half in the last 24 months because of automation overload. Email inboxes are a mess, LinkedIn is even worse, and AI tools are going to make this problem 100 times bigger. Yet most sales teams are responding by just doing more outreach!
4. Everything's lined up for a new go-to-market model. As cold outreach gets harder, the future will focus on warming up prospects through founder branding, innovative marketing, user-generated content, small events, and partner/affiliate channels. We're seeing close rates 2-3 times higher, sales cycles 60% shorter, and we'll need smaller sales teams.
5. The power of influencers is growing. As AI-generated content takes over, the most authentic content from trusted voices will become even more valuable. Social media is becoming the main way to create awareness, even for software platforms.
6. High-velocity environments attract better talent. The best people want to work on fast-moving teams. Nobody wants to be part of a bloated go-to-market organization that's just focused on headcount.
7. You can be profitable instead of predictable. Running a lean team that captures demand at the bottom of the funnel will improve capital efficiency. The key is resisting the urge to add outbound reps who just capture demand you're creating elsewhere. This reduces dependence on external funding and creates a more stable ecosystem.
8. Getting massive user numbers sets you up for global success. My friend Santosh always says that having 100,000 users equals a $1 billion per year marketing budget. I haven't pulled this off yet, but we're going to try with our B2B person-level identity product.

Go-to-Market

It's almost 2024, and the predictable revenue model is dead.

The next great startups will choose velocity and profitability over predictability.

This isn't just what buyers want - it'll create healthier companies with happier employees.

I'm calling this new approach "Inbound-Led Outbound," and everything's lining up for this to be the next big go-to-market strategy.

We spent $750,000 on three large trade shows trying to generate leads.

To be honest, I wish we hadn't spent a single dollar on them.

The Problem

The return on investment was minimal, and they consumed an enormous amount of time. The problem? Trade shows just don't work for us. There are too many people, and the environment is terrible:

1. The coffee is bad
2. The music is too loud
3. The lights are too bright
4. The food is terrible
5. The air conditioning is uncomfortable
6. The speakers drone on endlessly
7. There are too many pushy vendors

It's so bad that some brands actually walk around with their badges turned backward to avoid getting swarmed by vendors.

The Solution

We learned something valuable though: our company performs much better at small to medium-sized events where we control the guest list.

Our team has been perfecting this approach throughout the year.

First Steps

We started small, organizing dinners with other vendors where we both brought customers and prospects and split the bill.

Then we got creative and organized an "NYC Pizza Tour," taking prospects and customers to all the best pizza spots in New York City.

Scaling Up

Then we decided to go bigger. We wanted to create an event that fixed everything wrong with traditional trade shows.

Normal trade shows leave you exhausted and hungover, both physically and emotionally. We wanted the exact opposite.

Our Event

Last month, our Retention.com team rented a mansion in the Hollywood Hills.

We filled it with wellness experiences - breath work, cold plunge, IV and B12 injections, yoga, and sound healing.

We included fireside chats from known direct-to-consumer operators. It was invite-only - big enough to avoid feeling cramped, but small enough for everyone to talk to each other.

We topped it off with a sushi dinner and an amazing DJ party.

Results

The results were incredible:

1. Over 200 founders and brands attended (35 from our Top Accounts List)
2. Attendees had $2.2 billion in combined annual revenue
3. 64 Agency Partners and Sponsors participated
4. More than 20 Investors and Influencers joined
5. We achieved a 15.8% engagement rate (over 300% increase)

2024 Plans

We're going all in on these types of events in 2024.

This will be our go-to-market event strategy, not just for direct-to-consumer, but for business-to-business too.

Why?

Because real connections and community happen outside the convention center.

Conclusion

Sometimes the most expensive lesson is the most valuable one.

We lost $750,000 on traditional trade shows, but we gained a winning event strategy that actually works.