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Fixing the "Leaky Bucket" Problem

Entrepreneurship Lab · 2026-06-25 · 21 min

0:00--:--

Key moments - from our scoring

Substance score

29 / 100

Five dimensions, 20 points each

Insight Density6 / 20
Originality4 / 20
Guest Caliber9 / 20
Specificity & Evidence5 / 20
Conversational Craft5 / 20

Jason Kramer brings 25 years of business experience to explain why most companies lose 64% of potential customers through poor follow-up processes. He contrasts his first agency (project-based, inconsistent revenue) with Cultivize (retainer-based, recurring revenue), revealing how shifting from ad-hoc work to systematic lead nurturing transformed his business model. The leaky bucket metaphor describes what happens when sales teams lack a central system to track prospects, deadlines, and next steps - leads disappear when salespeople forget callbacks, proposals sit unsent, or context gets lost. Kramer advocates for either adopting CRM software like HubSpot or using his Profit Path tool (interconnected Google Sheets offering CRM functionality at minimal cost). He emphasizes asking "why now?" to uncover urgency and pain points, diversifying revenue streams beyond single services, and critically, delegating implementation work to focus on business development. Working with a skilled accountant and bookkeeper also emerged as pivotal for cash flow optimization and margin visibility - areas many founders overlook while chasing top-line revenue.

Key takeaways

  • →The leaky bucket - leads lost to poor follow-up systems - costs 64% of potential sales, making centralized CRM tracking essential regardless of business size.
  • →Shifting from project-based to retainer or recurring revenue models eliminates feast-famine cash flow cycles and provides predictable income.
  • →Asking "why now?" during sales conversations reveals true pain points and urgency, replacing generic proposal-writing with strategic discovery.
  • →Delegate implementation and execution tasks to specialists or offshore talent so you spend time finding new business, not doing delivery work.
  • →Hire a skilled accountant or bookkeeper early - not to save money, but to optimize margins, cash flow, and tax strategy in ways most founders miss alone.

Guests

Jason Kramer

Topics in this episode

HubSpotCRM implementationLeaky bucket problemLead nurturing strategiesProfit Path (spreadsheet CRM tool)Retainer business modelsSales follow-up processesCultivize (consulting firm)Delegation and hiringUpwork and Fiverr

Questions this episode answers

What is the leaky bucket problem and why does it cause lost sales?

The leaky bucket occurs when businesses lack a centralized system to track leads, follow-ups, and next steps. Sales teams get busy, forget callbacks, don't send proposals on time, or lose context on prior conversations, causing prospects to buy from competitors instead. Kramer notes 64% of buyers will eventually purchase if properly nurtured, but without a process, leads simply disappear.

What's the difference between Jason Kramer's first agency and Cultivize?

His first agency (16 years) was project-based - designing logos, websites, brochures - with revenue ending once a project shipped, creating constant cash flow stress. Cultivize operates on a retainer model, providing ongoing CRM consulting and software implementation, generating predictable recurring revenue and deeper client relationships.

What free tool does Jason offer to track leads without buying CRM software?

Profit Path is an interconnected Google Sheets system that replicates CRM functionality at zero or minimal cost, tracking prospect names, interests, entry dates, next steps, and conversation history in one place - ideal for startups unwilling to spend $50+ monthly on dedicated CRM software.

How can entrepreneurs scale faster by managing their time better?

Delegate execution and implementation work to others so you focus on sales, strategy, and business development rather than client delivery. Use tools like Upwork or Fiverr for cost-effective talent, and resist the temptation to do delivery work yourself even if you enjoy it - three hours daily on tasks you shouldn't be doing stalls company growth.

Why is hiring an accountant or bookkeeper important for early-stage businesses?

A skilled accountant handles tax strategy, cash flow optimization, bookkeeping, and margin analysis - revealing whether high revenue actually generates profit. Most founders ignore this and handle finances alone, missing opportunities to reduce taxes, improve margins, and maintain healthy cash reserves.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

6 / 20

The episode surfaces a handful of real ideas - lead nurturing persistence, the 'why now' sales question, retainer vs. project models - but spends most of its 21 minutes on mutual validation and clichés. The ratio of novel claims to filler is low.

64% of people that are looking to buy something...will eventually buy at some point, if you educate them and you nurture them during their journey
one of the first questions you should ask them is like, why now? So when you're talking to somebody...What's changed? Why are we having this conversation today?

Originality

4 / 20

Almost every idea in the episode is a well-circulated staple: work 'on' not 'in' your business (E-Myth), follow-ups matter, hire a good accountant, diversify revenue. Nothing is argued from first principles or presented in a way that challenges conventional wisdom.

it's the cliche saying, but the time you spend in your business and on your business
money is in the follow-ups, not in a follow-up, one follow-up, but follow-ups

Guest Caliber

9 / 20

Jason is a genuine practitioner - founded and ran a design agency for 16 years, sold it, and now runs a CRM consulting firm - which gives him real operator credibility. However, the scale of his experience is modest and he is not a prominent figure whose depth of knowledge noticeably exceeds what any competent B2B consultant would offer.

I started my own agency, which I had for 16 years, and then sold that to start Cultivize
we're either selling them software, right, like a HubSpot or some of the CRM software. And then so we're also working with them on a continued basis

Specificity & Evidence

5 / 20

One statistic is cited (64%) with no source named, and a handful of tool names are dropped (HubSpot, Upwork, Fiverr). There are no client case studies, no revenue figures, no conversion data, and no named company examples beyond the guest's own firm.

the statistic says that 64% of people that are looking to buy something...will eventually buy at some point
it's called Profit Path...it's interconnected spreadsheets built on Google that allow you to basically use all the functionality of a CRM without having to buy a CRM

Conversational Craft

5 / 20

The host regularly inserts lengthy personal commentary and affirmations rather than pressing for depth, and there is no meaningful pushback or follow-up probing on any claim. Questions are open and generic, and the interview ends abruptly with an audio cut-out.

I love that. So, guys, if you're listening, write this down. I think if you take one thing out of this, why now?
Yeah. And a question came to my mind. Maybe I'm jumping a little bit, but I have a lot of guests who build a business and then sell

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Most-used words

love15jason11different10sales9today8businesses8hire8sure8thank8back8build7project7revenue7system7advice7money7

Episode notes

Why do so many businesses invest heavily in lead generation only to see opportunities disappear before they become customers? In this episode, I sit down with Jason Kramer, founder of Cultivize, to uncover the hidden reasons sales funnels leak revenue and what business owners can do to fix them. Jason shares his process-first approach to growth, explaining why technology alone won't solve your sales problems and how aligning your sales, marketing, and customer journey can dramatically improve results. We dive into the "5 Why's" framework for diagnosing conversion issues, the key to getting teams to actually adopt new processes and technology, and how to perform a simple tech stack audit to identify tools that are costing more than they're contributing. If you're tired of losing leads, struggling with team adoption, or wondering why your growth efforts aren't delivering the expected return, this episode is packed with practical strategies you can implement immediately.

Full transcript

21 min

Transcribed and scored by The B2B Podcast Index.

Hello, everyone, and welcome to the new episode of Entrepreneurship Club. This is your host, Nevena Vajalac, welcoming you once again to the podcast where we help you grow and scale your business. As always, we bring you expert guests, people that talk about specific topics, their hands-on experience. And today with me, we have a guest from New York.

His name is Jason Kramer. And Jason is CRM email and sales process guru. He is a founder and CEO of Cultivize. It's a consulting firm specializing in lead, nurturing strategies, and done-for-you custom CRM implementation.

He has many years of experience, but we're going to talk about a specific topic today, something he really likes to explain well, and it's called leaky bucket problem and how to fix it. So let's welcome Jason to the show and we start this interview. Welcome, Jason. Thanks, Navehna.

It's great to be here. What a wonderful intro. I loved it. I mean, your bio is huge.

So I prefer to hear your story from you instead of me just rumbling and talking. So tell us, how did you get into marketing? How did you start it and why this area for you? And then we're going to dig in into entrepreneurship as well.

Yeah. So I'm going to make this, it's a very long story, but I'm going to make it very short for your audience so we get into the real fun stuff here. So I've always been a creative kid at a young age. I love painting, drawing, you know, building Legos, right, building things.

And so as I went through high school into college, I combined my love of computers into art. And so I became a graphic designer. I worked for agencies in New York City. And then in 2002, I started my own agency, which I had for 16 years, and then sold that to start Cultivize.

And so my background is kind of interweaved between being a like a data guy. Right. And like loving process, loving things organized and efficient with also my love of creativity. So it's a unique hybrid of skills that I bring to the world of helping businesses really connect the dots between their marketing and their sales activities.

Yeah. And a question came to my mind. Maybe I'm jumping a little bit, but I have a lot of guests who build a business and then sell and build another one. So how did you build business differently from your first business that you sold?

And in Coltewhite, what did you do differently? How is it different than your previous business? Yeah. Tell us a little bit about that.

I'm really curious. I love that question. So when I started my first business, I don't think I've heard of this term, but it's called a skillpreneur. And so my skill was I was a graphic designer, but I didn't know anything about owning a business.

I didn't know anything about profit margin, about sales. And so I learned, right? Like most entrepreneurs do, you learn by trial and error. And so the main difference between my first business and the second one is the first one was all project driven.

People would hire me to design logos, build websites, design brochures, all these different types of projects. But once the project was done, unless there was more projects that I was pitching to them or that they needed, sometimes the relationship would just end. And so I was constantly chasing revenue and constantly having the cashflow problems that a lot of businesses have is always making sure that we had a lot of projects to work on. And so you could, as imagine, it's stressful, right, to have a business like that.

And so in Cultivize, the business we have today, we're on more of a retainer model with our businesses. So we're either selling them software, right, like a HubSpot or some of the CRM software. And then so we're also working with them on a continued basis. So that's the biggest difference is that we found ways to provide continual value to our clients for years rather than just building a project, delivering it and being done.

And I think many, I mean, including me, many of us, we look for a skill and something we're good at. And basically we don't own a business, we're just self-employed because if you don't have a system employees, I mean, I'm not saying that was your case because if you build a company, sold it, maybe you created a system I mean, you had more people working for you. But if it's a project to project, like you said, it's starting something from being self-employed, which is absolutely fine.

And many of us really enjoy. It's fun. You know, you have a little bit of flexibility with your time. You can choose your clients.

But it's very stressful. So what is your advice in this? And I'm sure the success of Second Business came from that experience. And how can entrepreneurs maybe find that gap or something they can provide that, like you said, it's more like a long term for clients and they can have ongoing revenue and sales?

Like what happened for you? What did you say Hey this is what we should actually be doing and selling after so many years in your first company So that a great question And this is going to be different for everybody listening, right? Because everybody's have different businesses. But what I would say is that if you can diversify how you're making money.

So in other words, maybe you're selling one service to your customer base. Well, there's something else you might be able to sell to another customer base. Maybe you have, you know, you can work on a book or maybe you have like an online course you can sell. And so if you can diversify how you make money, that allows you to adjust your pipeline.

So you're trying to always keep different buckets filled. And so like in my world, for example, you know, in the beginning, we were just selling CRM solutions that companies didn't have them. But then I quickly realized that there are a lot of companies out there, even probably more so, that already have tools. They're just not using those tools very well.

And so we started consulting and saying, okay, well, we're not suggesting you get rid of what you have and buy new software from us. We'll help you fix the software you already have. So that became a secondary revenue stream. Another revenue stream for me today is I do guest speaking.

So I get, you know, I was just doing a keynote last week. So I get invited to do events. That's another revenue stream. So as you build your business and you build your brand and you're more desirable, there's more opportunities to generate revenue in different ways.

Yeah, I love that. Thank you for sharing. I think that's a great advice and a tip. And, you know, way to look at the things and look into what else can we do.

Not necessarily, like you said, create a software or CRM, but we can fix the existing. We have the knowledge. We can provide this. And yeah, I think listeners can definitely use that in adjusting their industry and their business.

So tell us about leaky bucket. What is the bucket? What is leaking out of bucket? How can we fix it?

So talk about this, because I think it's a very interesting concept. And I would love listeners to also hear it. Sure. So it all starts with the premise of this one statistic that I absolutely love.

So the statistic says that 64% of people that are looking to buy something, it doesn't matter what they're looking to buy, will eventually buy at some point, if you educate them and you nurture them during their journey. So in other words, if I'm looking to buy a car, I may not buy that car today, but I might buy it in six months. And if the dealership is giving me information, they're putting me onto an email campaign, they're calling me every couple months, checking in, I'm more likely to buy it from them because they're helping me make that decision.

And so the leaky bucket is when you don't have a process to follow up with all of the leads you're getting for your business, whether that be a dozen leads a month or 2,000 leads a month, especially 2,000, you need to have a process. And so where the leaks happen is when people get busy. When I say people, the sales team gets busy. And so they don't get back to people right away.

or someone says, call me back next week, but you don't write that down. You forget to call them back and then they just disappear. They buy something from your competitor. And so this happens way too often.

And why does it happen? Because there's not one central system that is keeping track of everything in your sales funnel, right? So in other words, who that person is, What are they interested in? When did they come into your system?

What is the next step? What are the prior conversations, right? You need to have all these different pieces in one place. If you're small, if you're just starting out, you can have it in a spreadsheet.

In fact, we built our own very, I want to say it's sophisticated, but it's extremely easy to use. It's called Profit Path. And I'm not here to promote it and sell it or anything like that. And in fact, I would give it away to your audience and we can talk about that later, but it's interconnected spreadsheets built on Google that allow you to basically use all the functionality of a CRM without having to buy a CRM.

Right. So you're really, really just starting out and you don't want to even spend $50 a month on a CRM. This would be a great alternative. And so that's where the bucket, you know, tends to have all the leaks is the process.

quite frankly, Nevada doesn't even exist. Yeah. Yeah. And I heard before, and this stuck with me, and I also use it all the time, like money is in the follow-ups, not in a follow-up, one follow-up, but follow-ups.

And for example, you know, like somebody selling an alarm system for houses, you don't maybe feel like you need an alarm system, but if your house gets robbed or your neighbor's house, you're going to be like, hey, I want to put this alarm system. And then if there is out of 15 companies in the neighborhood or in the town, one is following up or constantly present, constantly doing marketing, people buy what's in front of them. Most people have to go on Google to even find one company in an industry if they not familiar with it because many businesses I just feel are not so very well following up Like you said the market is leaking and they losing so many leads And I think it's so important in sales to understand that customers might not buy today, but they will buy, like you said, 60% will buy at some point in time.

So that's very, very interesting. Yeah. And you could also think of it as like the consumer. So for the listeners here, you're probably renting a home or you own a home.

You've probably had to hire a contractor or something at some point in your life. How many contractors did you have to call before one called you back? And then when you actually spoke to a couple of them, how many said they'll send you a proposal tomorrow and never did? That's the leak.

And so as a consumer, you know, well, I'm not going to, if I can't trust them to call me back or to send me a proposal, how am I going to trust them to do the project that I need to hire them for? and so you're going to go hire somebody else and so you feel like they're not interested to do the job and i'm like do you want to even do a job i don't understand i never understood this i love sales and i understand how important and by the way i i cannot say maybe i can say hate proposals in a way and when companies like oh go back and send me proposal and i'm like you know i can write like 10,000 pages and now we have chat gpt that can write me in five minutes a proposal but isn't the best to sit with the client and really listen what they need um i think that would be the best hey what do you need in what time frame how much we can invest how much you know what materials like if it's construction we can use so i think that's a great example and you're absolutely right like so many companies are not even you know people reach out to you and you take a week to send the proposal i mean who will wait how long do they have to wait for construction to happen if They're waiting for one week for a proposal.

There's another great question. And those questions you asked or mentioned are great. The one I would add to that is why now, right? So when you're talking to somebody, if you're in a sales role or you're the owner of a business or you're a startup and someone's talking to you about buying something from you, one of the first questions you should ask them is like, why now?

You could have hired someone like me a year ago or six months ago or five years ago. What's changed? Why are we having this conversation today? And when you ask that question, it starts revealing the true pain points of what's going on within the organization that you could dial in on and help them with.

I love that. So, guys, if you're listening, write this down. I think if you take one thing out of this, why now? Ask clients whatever it is that you're doing, a fitness instructor, a construction worker, a coach, whatever, a speaker, right?

Like Jason, like, why now? Why now you want to hire a speaker? Like what is exactly what you need? And I love that.

And then you will see how much urgency there is and pain points. So what incredible advice. So Jason, in building your businesses, if there is something you can go back, I love to ask this question because I think it's so powerful. And sometimes it's much more simpler than we think.

if you can go back in time and there is one thing that you wish you just knew earlier that would help you scale so much faster what was it for you what was for you like hey i should have just been doing this much earlier and this helped us get more customers and more business well i think there's a few things there but the one thing that probably is the most obvious that a lot of especially smaller businesses or solo entrepreneurs wrestle with is the time you spend and it's the cliche saying, but the time you spend in your business and on your business.

And so what that really means for the listeners, and I know you know that saying, but is how much of your time, if you're working eight hours a day, how much of that is spent actually doing work for your clients versus finding new business? And so one of the challenges when you're starting out is delegation. And now with, yes, tools like AI, which allow you to do a lot of the busy work, depending upon what you need done. There's talent all over the world.

So if you can hire somebody locally, if it's expensive, you now have access, you know, tools like Upwork and Fiverr and all these other tools that you can go hire people that are doing amazing work that are going to be more cost effective. And so the options are there. And so one of the things I would say is get out of your own way. You know, if you're being, if you're really good at selling and having those initial conversations and doing the strategy or, you know, whatever it is you're doing, then move aside and bring someone else in that can actually do the implementation work.

Now, granted, if you're like a home chef or like a personal trainer, right, then that's not as easy to do, right? Until you could actually then hire people, right, that you could teach and train and they could be personal trainers under you. And then you are just finding new business to the same way a gym model would work, right? And so that the advice I would give to younger Jason is you know is to do that And then the challenge you have right is another factor which is you may love doing it I was a graphic designer for many for 25 years I still like design.

You know, I don't really do it as much anymore. So my challenge was in my head, I would say, okay, yeah, I can give this to someone else on the team, but I'm really excited. I want to get in there. I want to do it myself.

Right. Or it'll be quicker for me to do it then to explain it to somebody else on the team and have them do it. So, you know what, I'll just do it myself. And next thing you know, three hours out of your day is gone doing something that you really shouldn't have been doing.

I love that. And it's like refreshment, you know, because I also heard before from my mentors as well. And like, don't spend time just in your business, spend it on your business. And it was so great to hear it again, to be honest, because we kind of get caught up in like every day and tasks and doing so many things.

I think it's such a valuable advice. And it's so true and like again we have passion we start some business because we love doing certain things and sometimes we think we are doing the best or we're just excited to do the project but at some point we are stopping ourselves from growth and I think that's that's so valuable so as we are wrapping up I want to ask you maybe some other important advice or something you think helped you as an entrepreneur that can help others? And maybe something that we didn't mention when it comes to building a business.

So one thing that you also should look at too is working with a really good accountant and even if needed a bookkeeper, because I think a lot of businesses think that they can handle the tax responsibilities and the financial responsibilities of that business on themselves. And they may be doing that to save money. They may be doing it for different reasons. But I can tell you that when I shifted for a long time, I had worked with, you know, now I'm almost 50 years old.

But when I started, I was in my early 20s, you know, on my own as a business owner. And so my father was like, use my account, he can do stuff for you. I'm like, okay, sure. You know, and he was okay.

He wasn't amazing. But he did like the bare minimum, you know, of what I needed. And it wasn't until I found somebody that really understood the nuances of the type of business I had. And it made a huge pivotal change.

I mean, it helped with cash flow. It helped with tax filing. It helped with so many different things, bookkeeping. And I would say that's something you shouldn't ignore, especially when you're starting out, is to make sure that you have somebody that is on your side to handle those aspects of your business.

Yeah, I absolutely agree. And thank you for mentioning that. And I think a lot of entrepreneurs, you know, numbers are not our favorite thing. It depends.

But I think a lot of entrepreneurs and then we just think it's not important, but numbers don't lie. And sometimes we're getting business, but there is no profit. So, you know, what's the point of generating huge revenue if your margins are low? So I think it's such a great advice.

And I think, yeah, usually at the beginning we try to save money. But what I love also about having a good team, an accountant, a bookkeeper, because they can also, you know, kind of call you out. Like, no, you don't do this with your money anymore. Like, stop doing this.

You're not allowed to spend money or you have to give 20% or these expenses are coming. And I think that's so important to have someone on your team that's going to be a little bit strict on you. And I think that's so, so valuable. So thank you, Jason.

really for such a great interview for sharing your knowledge. I really enjoyed. You're welcome. Navina, your audio just cut out.

I don't know. All right. I hope you can hear me. So I was just saying, thank you so much for being here today.

And I am very grateful. I enjoyed the interview. I'm sure the listeners also, I will get so many tips. And thank you for your time.

Thank you so much for being. I appreciate the invite again. Thank you guys for listening. We really appreciate you.

We appreciate our listeners growing as well. Make sure to give us some likes. Hearts, download the episode. Let us know what would you like to hear next in the podcast, who we should bring on the show and which topic we should discuss.

And as always, share with at least one more entrepreneur that can benefit from this episode. But Jason has something else to say. So I want to let him- I don't know if I mentioned, you could find me at afterthelead.com.

You can be on social and there's some free giveaways and different tools that I'll share with your audience if they visit that page. Amazing. So there are special guests for all of you who stayed listening to the end. So special gratitude for all of you who enjoyed.

Thank you, Jason. Jason is giving you a gift, a freebie, something that you can use in your business. And we're going to put it in the description of the episode as well. And make sure to tune in to the next episode and share this one with at least one more entrepreneur that can benefit from the podcast.

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