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Index/Marketing/The Makeshift CMO
The Makeshift CMO artwork

The State of Prop Tech & How You Can Take "Agency" Tactics and Scale it into a Specialized Mar Tech Company

The Makeshift CMO · 2022-11-26 · 50 min

0:00--:--

Key moments - from our scoring

Substance score

35 / 100

Five dimensions, 20 points each

Insight Density8 / 20
Originality6 / 20
Guest Caliber7 / 20
Specificity & Evidence8 / 20
Conversational Craft6 / 20

Rent Sync exemplifies the transition from agency services to specialized SaaS in the property management space. Joshua Lipton walks through the company's evolution from basic website development to full-service marketing agency to software-driven CRM and lead management platform serving Canadian institutional and independent landlords. The conversation reveals how Rent Sync navigated vertical integration by recognizing they were getting squeezed at both ends of the value chain - acting as mere data providers between property management software and listing sites like Kijiji, Zumper, and Rentals.ca. Lipton's background moving from larger organizations (Minto Group, RBC) to smaller startups (Postalgia, Rent Sync) shaped his philosophy on data-driven decision-making and sales-oriented storytelling. The episode covers how Rent Sync uses proprietary rental market data to create content marketing (podcasts, reports, blogs) that positions them as thought leaders, and discusses the shifting Canadian rental market dynamics - rising vacancy, rent control implications, and declining turnover - forcing landlords to shift messaging from price competition toward amenities and space. Future plans include deeper leasing workflow automation, virtual tours, credit checks, and predictive analytics around tenant renewal patterns.

Key takeaways

  • →Rent Sync evolved from website development → marketing agency → software platform by recognizing it was getting squeezed as a data provider between property management software and listing sites, necessitating vertical integration.
  • →Sales and data-driven storytelling are key to getting stakeholder buy-in for marketing budget increases; combining hard data with narrative persuasion is more effective than gut-feel recommendations.
  • →In contracting rental markets, messaging should shift from price competition to lifestyle positioning around space, amenities, and quality of life rather than rate discounts.
  • →Content marketing and thought leadership through data insights (reports, podcasts, blogs) became more effective for B2B property tech companies than direct marketing channels like Google Ads in the multifamily space.
  • →Successful scaling requires marrying marketing with operations/leasing functions end-to-end, from lead generation through lease signing and tenant renewal prediction, rather than treating them as separate departments.

Guests

Joshua Lipton

Topics in this episode

Vertical integrationZillowProperty management softwareRent SyncMultifamily marketingKijijiZumperRentals.caApartments.comCostar

Questions this episode answers

What made Rent Sync pivot from an agency model to building SaaS software?

Rent Sync realized it was being squeezed at both ends of the value chain - acting as a data provider between property management software and listing sites like Apartments.com and Zillow. Rather than expand geographically to the US (where Costar and Zillow dominate), they chose to deepen relationships with Canadian clients by expanding vertically into CRM and lead management services.

How does Rent Sync use its data to drive marketing strategy and growth?

Rent Sync leverages its large database of Canadian multifamily properties and market trends to create content marketing (podcasts, monthly reports, blogs) that position the company as an industry thought leader. This data-driven content strategy proved more effective for B2B lead generation than paid channels like Google Ads.

How should property managers adjust marketing messaging as the Canadian rental market softens?

Rather than competing on price, landlords should emphasize space, amenities, and quality of living. With increasing vacancies and rent control limitations, messaging should highlight three- and four-bedroom units, area benefits, and lifestyle factors rather than rental rate discounts.

What operational functions does Rent Sync want to integrate into its platform beyond marketing?

Rent Sync plans to add virtual tour capabilities, automated credit checks, lease generation, and predictive tenant renewal analytics. The goal is a full-stack platform connecting marketing, leasing, and tenant lifecycle management into one seamless workflow.

Why did Joshua Lipton believe sales experience made him a better marketer?

Lipton saw that both sales and marketing require getting the right information to decision-makers to change their minds. Sales training taught him how to articulate data-driven arguments persuasively, which he applied to securing marketing budget increases and driving internal alignment.

What our scoring noted

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

Insight Density

8 / 20

There are a handful of genuinely useful operational observations - the vertical-integration squeeze, Canadian rental market seasonality and the luxury-unit-first contraction pattern - but the bulk of the episode is career narrative, generic startup advice, and host filler. The density of actionable insight per minute is low.

anytime there's a contraction, it's the higher end that gets hit first
we saw that we were getting squeezed on either end. We were just becoming a data provider

Originality

6 / 20

Most of the frameworks offered are explicitly borrowed and well-circulated (the HBO/Netflix quote, 'do things that don't scale', the 100-ideas exercise), and the career advice (say yes young, say no senior) is standard. The niche Canadian rental-market observations are the only meaningfully fresh content.

I can't remember who said it, but there's a great phrase which is when you start out, you really have to do the things that aren't scalable
there's a great quote, I think it was, uh, Netflix, uh, versus hbo. And, uh, the CEO of HBO said we have to become Netflix before Netflix becomes hbo

Guest Caliber

7 / 20

Josh is a genuine practitioner - Director of Product & Operations at a ~75-person Canadian proptech company with real startup experience - but he hasn't operated at notable scale and his insights reflect a mid-career, mid-market operator rather than someone who has built or run something exceptional.

I'm the director of product and operations
probably the most stressful year of my life, um, to that point. But it was also where I saw the most growth

Specificity & Evidence

8 / 20

The episode names specific competitors (Costar/apartments.com, Zillow, Zumper, Rentals.ca), gives a concrete rent-control figure and seasonal demand pattern, and illustrates the 'say no' point with a real Postalgia deal worth ~10% revenue. However, many claims remain vague ('a lot of demand,' 'very large percentage') and company metrics are almost entirely absent.

your landlord can only raise rents 2.1% I believe next year
August is typically the hottest month. And then September you see a big drop

Conversational Craft

6 / 20

The host provides reasonable topic structure and occasionally steers back to relevant themes, but almost never pushes back on a claim, frequently summarises rather than probes, and peppers the conversation with low-value affirmations that interrupt flow without adding depth.

That's awesome. That's amazing
Very good example

Conversation analysis

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

Share of words spoken

  • Speaker B78%
  • Speaker A22%

Most-used words

marketing43sales28data28product26market20start18sometimes18better18sure17back16clients15software15tried14listing14value13rent11

Episode notes

In this episode, Bruce has on Joshua Lipton, his buddy from the Prop Tech world who has transitioned from marketing, to sales, to Director of Product & Operations at Rentsync, which turned from a Marketing Agency to a Prop Tech, SaaS company that is a leader in multifamily marketing software & services, with 20000+ properties on the platform and over five million leads generated annually. As we go on this episode, Josh and Bruce geek out over the prop tech market, talk career changes and talk about the differences between true SaaS GTM and how to transition out of an agency to a repeatable, SaaS model. "It's never going to be perfect. But I'd rather have a really good product 85% of the way there today, than a 100% perfect product 2 years from now." Josh Lipton, Rentsync: Read about how Rentsync is disrupting to the prop tech/long term rental space:

Full transcript

50 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: Foreign. Welcome to the Makeshift cmo, a, uh, startup marketing podcast for founders and early stage company teams. All right everyone, welcome to this edition of the Makeshift cmo. My name is Bruce Chen. As always, today I'm joined by a very special everyone's special guest, uh, Joshua Lipton. Uh, Josh is helping the multifamily industry get more out of their marketing. And if you haven't guessed, Rent Sync is a martech platform, uh, for real estate multifamily owners. Uh, Josh and I came across, uh, a while back when he uh, was trying to sell me Postalgia for another sales and marketing campaign we were running at a different company. Um, but I uh, think it's uh, I think it's always good to get companies on who are in an interesting space like Proptech, but at the same time have sort of expanded uh, to different solutions in this market. How are you, Josh?

Speaker B: I'm doing well. Been a while, uh, but so good to hear from you Bruce and good to see you. Thanks for having me on. Really excited to have this kind of discussion.

Speaker A: So as I was talking with you in pre show, uh, Josh has a varied background of uh, starting from, I believe you were at Minto Group as a marketing coordinator, then you went, uh, around to a variety of different, um, startups and sales and marketing, uh, roles. Did you want to just give everyone the origin, uh, sort of background story?

Speaker B: Sure, sure. Um, I mean I can go way back. So I mean originally I, to be quite frank, I didn't know what I wanted to do coming out of university. Uh, I was good at math, uh, but I also had some creativity. So I thought marketing was kind of the perfect blend of that. Um, and actually started at RBC as an intern. Um, that was just a couple months. Didn't uh, like it. RBC is a great organization, but it was, I was a tiny cog in a machine. Then I went to my next role, uh, which was at Reliance Home Comfort. Smaller company, still felt like a cog in the machine. And I just kept working my way down into smaller and smaller companies as you said. Then it was to Minto, um, which is one of Canada's uh, largest apartment building owners and they also do development. Um, actually liked it there, good culture. But again I found that I wanted to do more and I felt like my voice wasn't really being heard. You know, I would make recommendations and they go on deaf ears. Uh, so I continued to go down that ladder to smaller and smaller companies, uh, to what at the time was called Landlord Web Solutions, but is now Called Rent Sync, um, and I found my way there. At the time, uh, I think we were a group of 30, uh, so it was still a small company, um, and I really found a home there. It, um, again I personally like being able to really, um, not feeling like a cognitive machine. That's really the analogy I use. I really had a say in how this organization was run, uh, even from an early standpoint, um, though I did originally go into sales. Um, so I switched from marketing to sales, uh, which was a bit of a. Outside my comfort zone. But I've always been a believer that if you're not pushing the boundaries of your comfort then you're not really growing. And that's really what I've tried to do is I've tried to continue to push my comfort level, try, uh, things that are different. Um, and you know, I actually left Brent Sync temporarily, uh, and went to, as you said, Postalgia, um, which was an even smaller company that was one of four. So that was a true startup, as small as you can get and um, probably the most stressful year of my life, um, to that point. But it was also where I saw the most growth. Again, uh, it was completely outside my comfort zone in that I was the head of sales. We basically, if I didn't do sales, you know, the company was, who knows if we're going to make payroll next, uh, next month. So it was, uh, again we got the company on track. I've left the company since, but it's doing well and I think I left in a position, uh, for success. Um, and I still talk with the owners of postalgia. Great company. And again I learned so much, um, because again I was running it all from at that point m and actually made my way back to Rensync. At the time they no longer need someone in sales. Um, so I went into operations and now I'm actually on the operations side. So I'm a product, I'm the director of product and operations, um, over there. So it's both, uh, how the product works as well as some of the operational elements. Uh, but I still think that there's a through line here, um, to marketing, which has really always been again, it's how I started. Uh, first of all it's a marketing platform, rensync, so it offers marketing to multifamily, uh, clients. But on top of that I really do think there's a marriage between um, marketing and product. Uh, it used to be just here's our product and how do we get people to use it. Uh, but Today ux, uh, and UI is very much kind of the marriage between product and marketing and they really have to go hand in hand. So um, continuing to again, push my boundaries of what I feel comfortable in and I'm learning a ton. But uh, yeah, that's kind of a bit of background on me.

Speaker A: That's awesome. That's amazing. Um, I wanted to ask and sort of confirm I did some sleuthing on like what rentsync did before, what they seem to be doing now. Is it, is it uh, is it correct to say that they used to provide targeted, ah, marketing strategy for your uh, target audience, um, in an agency style, but now you guys have grown enough to the point where you're building SaaS and selling it?

Speaker B: Yeah, that'd be, I mean if you really want to go all the way back to the very beginning. It started as just a website development company. They just built websites for apartment building owners. Very small business. You know, that's nothing sexy. Um, but they slowly started expanding and going into ancillary services. Uh, so then it was okay, we'll send your property data out to different listing sites, uh, like Kijiji or Zumper or Rentals ca. Uh, and then as you said, then they started expanding to okay, let's become a mini agency. Let's start doing Google Ad services and ad management and branding. Um, and now we're really getting into more heavy duty, uh, software development, um, CRM elements, really trying to uh, manage people's data and allow them to automate, um, some of the daily tasks that property managers and marketers in the property management and development world would need to do. It's really about making sure that the data flow between, hey, you want to market that property, let's get that property, uh, the data out there, then let's follow the lead, track it and even help you book a, uh, showing and sign a lease. Again these are all things that we're building into the platform. But yes, it's definitely becoming more software heavy.

Speaker A: One piece I want to go back to and something that you've brought up that would really resonate with most of our audience. Um, first of all, not feeling like a cog in the machine, uh, but you were talking about you um, went from company to company, sometimes smaller, but uh, you had a say in how the company was run specifically as it relates to marketing. How did you get your colleagues to sort of buy in to um, the things you were doing for AdWords or um, to get more budget? Um, that's one of the biggest problems for marketers today, how did you sort of broker that for sure?

Speaker B: And I'll actually. So I was at, uh, the second job I had was at a company called Reliance on Comfort. They're an H vac company. And again I would make pitches after pitch and no one would listen to me. Um, and I actually think a big part of why I, how I learned to get people to listen is from my time in sales. Um, sales helped me. To me, sales is all about getting the right information to the right people's hands at the right time, uh, to help them change their mind. That's really all you're doing with sales. Uh, when you're in marketing, you still have to sell your ideas. You still have to convince people, uh, why you should go with direction A versus direction B, uh, why we should increase budget, why this is a good decision. And so sales really helped me articulate, um, the arguments that I was making and why one decision might be better than the other. Uh, but another thing is, obviously I am decent enough with math, um, that I really try to make data driven decisions. And so a combination of I think you need to have the right data. You can't just go out on a whim. Um, so I try to always bring data, uh, to make better decisions and back that up and then the sales. And I've tried to also improve my rating and to really say how do we succinctly tell a story here about what of these two options is better and how is the market changing? Why do we have to go in this direction or that. And it's really about again, using data to tell a story. That's really what I've tried to do throughout my career and uh, I continue to improve and get better, but that's really what people should do. And another thing I think maybe that uh, your listeners might be interested in is don't be afraid to try and be contrarian. Um, it's easy to say just keep doing the same thing. You know, I had, um, at a couple places that they were just doing the same thing month over month and no one wanted to change anything because it was easy. Um, but if you really have a good idea, if it's contrarian, um, people will listen. And um, yeah, so, so I've always tried to think a little outside the box.

Speaker A: I wanted to dovetail into the fact that again, we're on a podcast, uh, format most of our listeners probably can't, uh, see unless you're looking up Rent Sync's website. Um, but for a 75 person or so company. Um, there definitely seems to be a real investment in not just marketing, but content marketing. There's podcasts, there's blogs, there's guides. Um, you mentioned data and that sales and storytelling. Talk to me about, I don't know if you were there to see it, but how philosophically that this investment was going to be made in education and content. Um, because it clearly seems to come from the leadership side.

Speaker B: Yeah, so that's a big part of one of the changes we're making is we have this treasure trove of data. We have so many clients there. How do we use that to tell stories that are valuable to our clients? Again, our clients are institutional landlords and sometimes smaller, uh, landlords. But um, you know, they're interested in how the market is changing in terms of rental units, rental rates, vacancy, turnover. And because we have all this data we can actually tell that story. So we've tried to really utilize the data that we have, um, and again use content, whether it's podcasts, whether it's blogs, whether it's reports that we put out, uh, monthly, uh, to try to um, again tell a story that will add value to our clients and help them make better decisions. Um, so that's been a big part. Another part was again, uh, sales can only go so far. Um, you need to sometimes. Um, we tried direct marketing and Google Ads for our own services and it was not super effective. Um, as a B2B company, uh, it's a much longer sales cycle and so we had some success with LinkedIn ads. But Google Ads, there's not a ton of people searching for property management websites on a day to day basis. Um, so the content marketing was really a way to um, became a thought leader within the industry, get uh, our brand out there. Uh, people now know us and they look to us for um, insight into where the Canadian market, uh, rental market is moving. And again content is at the core of that strategy. So we've really made a decision to really invest in content. And again I've tried to back that up with data. Uh, some of it is just interviewing interesting people in the industry. Um, but I really think that a valuable part for our clients is the trends which you know and where the data is following.

Speaker A: Let's talk about that a little bit. At the time of recording we are 10-05-2022, uh, where there are not such great headlines in the news about uh, the state of the property market in, in, in Canada. Um, how do you find that? This, as someone who's working in proptech um, is for whether it's the marketing or operations or customer or sales team, adjusting the messaging and adjusting the strategy, uh, to the way that you're positioning, um, yourselves for sure.

Speaker B: Well, I will say the rental market in Canada over the last two years has changed so dramatically. You know, when Covid initially hit there was a ton of fear, uh, and there was actually very high vacancies and there was tons of, um, incentives to get people to rent. Um, then we had super low interest rates. Uh, then people who might be looking to rent instead chose to buy. Obviously house prices went up. Uh, now with interest rates going up, people are kind of forced out of the buying market. There's a lot fewer transactions, uh, in the buying market. Uh, and also rental rates are still very high. And so we're actually seeing a lot less turnover. We're seeing people stay where they are and, and not move. They're saying, you know what, I'd love to move to a two bedroom, but instead I'm gonna stay at the one bedroom because if I move, um, obviously there's, there's rent control in most provinces. Um, so you know, your, your landlord can only raise rents 2.1% I believe next year. But if you move uh, to a new unit, they can set it back to market rates. Uh, so yeah, we've seen a huge drop in turnover. Um, rental rates are still very high and it is starting to, uh, however, we are starting to see that ah, there's typically some seasonality, uh, no one really wants to move. Come, uh, winter time, it's much tougher to move in the snow and it's cold. And so we actually do typically see demand start to fall off, um, in September. Um, August is typically the hottest month. And then September you see a big drop, uh, through the end of the year until December. And then it's kind of picks back up in January. And we are seeing that. I actually just went over the data yesterday and so we are still seeing a somewhat of a demand fall. Uh, I still think if you are a smaller landlord, um, there's still a lot of demand there. But I am starting to see the luxury units, the purpose built, newer, uh, developments are starting to see a major slowdown there. Anytime there's a contraction, it's the higher end that gets hit first. And so we are really seeing that. And so, uh, these companies are having to change their marketing and having to adapt quickly, um, and they are having to start, you know, it was a bit of an easy environment for the last year or so where uh, vacancy Rates were so low that most places were getting rented. And we are starting to see that start pullback vacancies start picking up. And so you don't want to have to. The last lever that you should pull is market rents. Hey, let's drop our prices. We don't want to do that. So we're seeing people instead, uh, start focusing on the quality of living. People really wanted more space lately, so we're seeing three and four bedrooms, uh, going for much more because, you know, three and four bedroom apartments were not very common, but they're starting to become much more common because people just don't want to be crammed in a shoebox, but they can't really afford a house. Um, and so we're really starting to see messaging focused on space and the amenities and the area really pick up, um, in terms of how companies are positioning their products in terms of apartments,

Speaker A: uh, you can take exactly what Josh said there and apply it to any, uh, product or service in this time, where just about every single, uh, sector right now, no matter what you're marketing or selling, is being affected by the economy. Whether you know the service is living somewhere or it's some kind of other SaaS company, uh, the point that we want to take away from this is you got to change up your messaging, um, for sure. So my question, uh, next, as it relates to, um, rentsync, which is now, you could say it's proptech, but you could also say it's a marketing tech platform platform. So it's almost in. It's almost. You could almost put it in the same category as like a drift or a HubSpot for like a very small niche? Um, at what point, because you were there on two separate stints, where was the paradigm shift, uh, where they decided to say, hey, let's take it more from just, you know, landlord marketing web solutions to let's start building software and let's automate this thing. Um, I'd love to pick your brain on what that thought, operational thought process, um, was like, for sure.

Speaker B: And, uh, part of it was just, uh, vertical integration because we were finding that there's a great quote, I think it was, uh, Netflix, uh, versus hbo. And, uh, the CEO of HBO said we have to become Netflix before Netflix becomes hbo. That's when hbo, uh, so obviously HBO now has a streaming service. Netflix, uh, was getting into content. And that's all about vertical integration. And that's what we really saw, and that's why we made this pivot, is we saw that we were starting to get squeezed on either end. We were just becoming a data provider. And so people were just coming to us saying, hey, can you send our data to this listing site or that listing site? And there was a property management software on one end where we were taking the data in and they were sending out to listing sites and then they were feeding those leads back into another CRM. And we found that we were getting squeezed. And we actually have a very large percentage, uh, of the Canadian market. So our options were either to expand into new geographies like the states, or to start going down funnel or up funnel, uh, either, and really into some of those other services. So CRM and listing sites. And that's really what we decided we needed to expand. In any business, you have to keep growing and you have to expand that tam. Um, and so we tried in the states. Um, it's a much more competitive market and really we didn't have a foothold there. There's, uh, two big companies there. Costar, ah, which owns apartments.com and Zillow, which does. Obviously their big thing is home buying. Uh, but they're actually really big into the rentals because about 15% of renters are still kind of on the fence and they might buy. Um, and so those two companies make up a huge amount of, um, uh, the renter. So there's not a ton. A, uh, great way for us to get our foothold in. So we said, you know what, let's use our best asset, which is we have great relationships with our Canadian clients. Let's go deeper with them. Let's be more than just a data provider. Let's start offering CRM services. And yeah, so that's what we did. It's obviously a bit of a pivot, as you said. Um, but that's again, a key way is we just said we had to go vertical. We had to get more and more of the value chain because really we were getting squeezed on either end. And ideally we'd love to go full stack. We'd love to be. We'll collect your data, we'll send it out to the listing sites. We'll even have our own listing site. Uh, then we'll pull the data back in, we'll offer reporting, and then we'll, uh, allow you to contact people and manage your prospects in a CRM service. Again, we want to be full stack. We're headed there. We're not there yet. But that's really what the pivot was all about, was how do we grow our. Continue to grow our addressable Market I

Speaker A: want to focus on a couple things. Growing the addressable market and vertical integration. Um, again for those who might be unfamiliar, um, in, if you're listening from the United States or elsewhere in Canada, um, the way one looks for a condo, um, the amount of ways that, or, or a place to live, the amount of ways to do this has increased by a million ways. There's a million listing, there's a million listing sites, um, that out there. If you, if you try and search like apartment, ah, in Toronto or Vancouver, there are a million listing sites out there. And I think it was only a matter of time before there uh, was a Zillow or Realtor Ca or sorry, Zillow esque player that would come in and try and uh, um, integrate with those areas of the value chain. Um, so that's sort of how I see that. Um, the other thing that I wanted to touch upon there was um, no way I did touch upon that. Growing the addressable market. Um, yeah. So what's next for you guys? As you guys sort of expand into services, are you guys going to do m, uh different things? Like I don't know, like this is a wild thing, but maybe like an email marketing tool from within the platform or.

Speaker B: For sure. So right now we are really. So again we're working on some CRM tools and they're in uh, stages really the next steps, the next, let's say five years look like, let's complete that. Um, and then really what we want to do is go deeper into some of the day to day operational tasks that uh, connect marketing to uh, leasing. Uh, that's really where we see the biggest gap in the market right now is it's easy to generate leads, but um, then you hand it off to the leasing team and then the leasing team has to do a showing and there's always some confusion. So we really want to make it easier for people to book. Ever since COVID people really want to be able to either do a virtual tour, um, remotely, they want to, or they want to book a tour without having to talk to someone. So we want to make that, that much easier, uh, as well as make leasing easier. And uh, there's also just a lot of little things. Um, you know, the largest clients, Those big institutional REITs who own thousands of apartments, do have some software sometimes. But again it's our software has to talk to this software. We want to have it all in house and that way everything works seamlessly. But really we want to bring that down in size. So from the institutional landlords that are uh, you know, marketing thousands of units to someone who might only have 10 or 20 units. We want to still offer them that same value and so make it easy for smaller landlords to uh, automatically rent their, uh, you know, list their unit. Uh, then I get prospects, uh, send them a credit check, rank them based on their credit check report, uh, and then send them an email lease. Uh, and that way just make it that much easier to go from, again from start, which is the marketing all the way through to the lease. And really the way I see it is we want to continue that even after the lease in five years time. I want to be saying uh, which tenants are most likely to keep re upping. Uh, you know, hey, we see this uh, tenant is uh, or this lease is up for renewal. Do you want to list it now months in advance? Uh, we want to be able to know based on turnover rates and predictive, you know, when they should start listing it, how long it'll take to list and how long it'll take to sign what the rent should be. These are all down the line. We're not there yet. But really that's the goal is to really close that gap and be more than just marketing. The way I say is it's again, I almost think it mirrors my career where it's marrying marketing with sales in the apartment world and on the multifamily world. The sales side is the leasing. We really want to marry those two because I think too often they've been kind of uh, distinct entities and we want to really bring them together and make them both work, uh, in unison.

Speaker A: I almost feel like the rent Sync platform could be in some ways uh, analogized to, I don't know if that's a word, uh, analogous. It is now analogous to your career because um, here's something I want to ask is you have property managers, it's, it's B2B. Um, and you have a software platform and you know there, there are these services within the software platform, marketing, CRM. Uh, um, do you feel as a B2B software services provider that there's challenges with scalability because one property management company will want different things as another and so that sort of presents like challenges creating that sort of um, repeatable uh, product. Is that something, yeah, is that something that you run into?

Speaker B: For sure. And I also think, I mean this is maybe even something that's relevant to startups in general, which is this very big uh, push and pull between really making a customized solution for a client who has very specific Needs versus making something that's more. Hey, this is a generalized solution that works for a lot of companies. When you're small, sometimes you really want to get the client, but the client says, I need this, this, this. They ask for really custom things and so you have to come up with a custom solution for them, uh, that's not always scalable and it doesn't always work. And as you get bigger, you actually can kind of be pickier and you can kind of say no to clients a lot more. You don't need every little client. You can say, you know what, that's outside our wheelhouse. We aren't able to do that. And so you don't have to feel like you're pleasing everyone. Um, and so you do want to make customized solutions. We don't want to make. Rensync is not an out of the box cookie cutter. But sometimes clients ask for very customized things and we just have to say no. And so we try to balance making something that's scalable and that uh, again, scalable means easier to continue, uh, to build and grow and works for everyone and better margins as a business ourselves. Uh, and we want to balance that with customizable. We want clients to be able to customize their own account. Um, so just as an example, uh, companies can change their ad titles based on how they want to. So you can either go with our defaults or, or you're able to say, you know what, I want the ad title to not be a call out, like beautiful two bedrooms. I want it to say, you know, just um, beautiful two bedrooms in city. Um, so you can kind of use more, uh, you can use some technology to say, uh, change up the marketing based on each and every listing. So we really try, sorry about that. We really try to balance that push and pull between making something customizable that works for, uh, a specific client and something that is scalable and a great service for everyone.

Speaker A: Well, you just described, and I'm putting you guys in good company, but you just described the value of what Airbnb brought to their, um, their target audience, which, um, you know, if you think about hosts, yeah, 99 of hosts are not going to be digital marketers, right? So, ah, so when they put up uh, listings, uh, they needed like, they're like, what do I name my listing? You know, they're going to need a bit of a playbook. So now that's why every, every Airbnb listing, you know, reads the same. It's like comfortable two bed. Uh, that's why they all read the same, um, um, but they helped the landlord, uh, get to the top of their own sort of search engine. So, uh, I find a lot of, uh, insight and uh, what you just said, uh, right there. What's an example?

Speaker B: Let me jump into Airbnb real quick just before we move on, because I think it's a really interesting company and I think one of the biggest things it's done, and I think this is one thing that kind of we're trying to add in as well, is the factor of trust. Um, you know, I don't know about you, I used to rent cottages, uh, for a weekend with friends on, um, various, uh, sites. And you just have to trust that someone say, send me an E transfer or a check or bring cash. And I'd have to trust that I'm actually going to get what they said it was. And Airbnb really made it trustless. Uh, you put down your credit card, they hold it. If there's any issues, they'll refund your money. Uh, and we really want to move towards that. It's a bit of an off topic thing, but we actually have seen an uptick, uh, in scams on other sites. Um, again, we try to add technology to make sure that, um, renters are knowing that our listings are verified. We're working with institutional landlords, um, but there has been an uptick in people posting non legitimate listings, uh, and then asking, hey, can you send me a deposit? And so I really think Airbnb has done an amazing job of, um, building trust between both the hosts and with the renters. Um, obviously it's a bit of a different industry with short term than long term, but I think they've done a great job and I think that, uh, the rest of the industry is taking notice of that for sure.

Speaker A: Very good example. One interesting point you made earlier, um, and this is something that, um, for our listeners that are founders building any type of SaaS product, there's always that balance, ah, between, okay, I want to sell something that's scalable versus the customer is asking us to build this customized solution right now. There's money on the table right now. What's, um, an example of a, uh, situation or a product that you maybe had to say that you know of, that you maybe had to say no to, that you might think, you know what, that actually would have been pretty cool, but you had to say no because it's like not really scalable, for sure.

Speaker B: Well, um, there's been a lot and they might be a little minute, you Know, I don't want to call any clients, but I'll give one that's not related to rensync. It's actually related to the company that I was working at when we first met, postalgia. So for the listeners, postalgia uses, uh, robots that hold pens to create handwritten co cards. Um, and so we worked with a lot of nonprofits, political campaigns, and actually the area that we grew the most into was real estate. Just, uh, so happened that I had a big background and I thought it made sense. You know, it was more on the sales side. Um, but again, it goes back to trust. I always thought that a handwritten note, uh, builds trust immediately with someone reading it and so has a higher open rate. Um, but we had a client who asked to write on a very odd shaped card, and it just wasn't scalable because the way the robots work, it feeds in a card and then it writes it. And these were massive pens. And it was going to be a deal worth something, like, grow our revenue by 10%. This one deal. And it was a. So it's not insignificant, right? Uh, pretty large deal. And we just had to say no, because operationally it would have completely ruined us. We would have had to retrofit all of our machines, and it just wasn't doable. So we had to say no. Um, but again, I will also say to all founders, you know, the number one thing you have to do always is stay in business. Uh, if you are going through tough times, you have to extend that Runway. And so sometimes you do have to take deals that you don't love. Um, but it's really about balancing and where you are in that, uh, really where it is in that stage. I can't remember who said it, but there's a great phrase which is when you start out, you really have to do the things that aren't scalable. Um, whether that's, you know, reaching out to each and every customer and just getting feedback, talking to them, making sure everything went well. As you grow, that's when you start scaling. So when you're small, sometimes you have to do the things that aren't scalable. Uh, but as you grow, that's really when you start becoming pickier and able to determine, uh, hey, is this revenue revenue? Not all revenues built the same. Also, some revenue is great and high margin and easy, and others is this is going to take a ton of work to make it work and it's not scalable. And so you really just want to make sure that any deal you're Doing based uh, on your stage of your specific startup. Um, does this deal make sense to take on? I'm a big believer in firing the client. Sometimes, sometimes clients are just not worth it. They're headaches. They are canceling, uh, stuff and just not worth all the time and effort you really have to grow a business. So yeah, that's one thing I've definitely learned.

Speaker A: It's really funny because the guy I met you with, uh, Aaron, uh, who we were running that campaign with, uh, he and I on this podcast also talked about an instance of that. It was obviously a completely different context, but I find that to be funny that way. Um, yeah. How do you. There's one theme, uh, that you go on there when you say sometimes you have to follow fire the client or say no to things. Um, let's bring it back to the early stages of your career where you know, whether you're in marketing and sales at an early stage startup doesn't um, matter. Uh, holistically, probably the biggest issue that you'll have is saying no to doing things. Um, because what I find is once you learn to say no to doing things and focus on the high value things is when you're creating career, um, or your product or whatever takes off. Um, but it seems like you figured that out. How did you reach that point in your career?

Speaker B: For sure, I've actually found. So when I was, when I was young, I didn't want to say no in my career. Still think I'm at heart. I, um, didn't want to say no to anything. I want to say yes. And part of it was because I didn't know where I was going. I had some thoughts and I said, oh, maybe I'll do this, maybe I'll do that. Um, but again, do you want to try sales? I didn't say no. I said yes. And so really when I was younger, I say yes to everything. And um, it is not about focus at first. It's about trying a bunch of things and seeing what you're really good at. And that's really what I want to find out is what am I excellent at and what can I do better than 90% of other people? And so I said yes to a lot of things and a lot of it I wasn't great at. I will admit I was a, I always say this, I was a mediocre salesperson. Um, but I tried to focus. What was I good at at sales and what was I not good at? And what I was good at is I was good at talking to people I was good at using data to tell a story about why a product might be good. I was not always good at the close. So I said I'm not good at sales, but maybe I'm good at, um, what else uses the things I'm good at. And so I tried to say yes to other things that were related to that. Uh, now that I'm, uh, more senior and a little again, I'm still early in my career. But now it's all about saying no to things. It's all about focus. That's what I've really learned is at first, I think you want to say yes to everything. Uh, I try to analogize it to, I'll use your word, uh, to dating. Uh, when I first started dating people, I just said yes to every date. And I went on some good dates and I went on some bad dates. But as you get older, you know what you're looking for in a partner. Uh, and so you can say no to a lot more and find better dates. And so that's really what I've seen. Also my career, as I've gone, uh, further along, I've said no to a lot more things and really said I need to focus on the few things that add the most value. Uh, you know, I really find this. I still want to take on a lot, but it's a lot about delegating. I can't do this or someone else can do this 80% as well as me, and I need to do this. That I'm five times better than everyone else at the company at, uh, and so I need. My time is best served here. So, you know, I'd love to. We're working on a marketing campaign coming, uh, up, an email marketing campaign. I would love to write all the messaging. I'm not going to do that. Deep down, I really want to, but I'm going to hand that off to someone else. I'm going to review it before it goes out and make some tweaks. Uh, but I'd love to do it. But I say, you know what? I have too many other things on my plate and I really need to focus on those important things. And this other person's 90% as good as me at writing copy. So I'll let them do it. Maybe they're even better.

Speaker A: So with that philosophy, how did that lead you to where you are more on the operations side?

Speaker B: Yeah. So as I said it really, I tried to find the through line in what I was good at and what I liked. And I think sometimes Those go hand in hand. Uh, I always used to wonder, you know, am I good at, do I like something because I'm good at it or vice versa? In other words, you know, I think most people like being really good at something that they do. They like taking pride in being great at something. And so I said, if I'm great at something, I'm going to like it, and if I like it, I'm going to work harder at it. And if I work harder at it, I'm going to just get better at it. And it's going to be this virtuous cycle of, um, just getting better and better at something. So I tried to find those things where I was really good at them and did like doing them so that I could continue to get better. And so that through line again was from marketing to sales, it's about, uh, you know, working with clients. At the end of the day, sales, uh, is still about working with clients, but it's not about a broad message to everyone. It's working one on one. And then from sales, uh, to product marketing, it's kind of uh, or to product development and operations and it's bringing back kind of that broadness. So it's speaking one to one, but to everyone. So it's how do we customize the uh, site or the software to allow you to do what you need to do and tell a story and allow you, give you the tools and how do we tell you that you're going like, what is most valuable to you, what is really the value prop? And so then marketing has to do a job of describing that value prop, but product's really about creating the value prop. So again, to me it's really about understanding the client, understanding their behavior, understanding where they're deriving value, adding, uh, that into the product and then working with marketing to tell that story. And that's really what I've tried to do and evolve is really again take that element of marketing that I really like, which is understanding the end client, um, but bringing that into what adds value. How do we add that into the product?

Speaker A: Awesome. So I want to take one thing away for, uh, people out there who are startup marketers, um, who you know, are good at the things that Josh is, is good at. But maybe, um, they feel like they're a square peg in a round hole based on the product or whatever situation or company that they're in. But again, just that process of focusing on what are you good at, what are you maybe not that good at, and then, uh, sort of you know, working your way into, into a better situation. Which again, for early stage marketers and startup founders is something that they're always trying to do with their products.

Speaker B: Uh, and I actually think it's really important to. No one wants to admit that they're not good at things, but I think it's really important because when you're not good at something, it helps you. Again, you still need someone to do something. Hey, I'm not good at engineering. I'm not good at the software side. So I work with someone who is amazing at that and they're amazing, uh, software manager and they understand the tech and together I can tell the story and he can translate that into code and work with our development team to make that real. But I think it's really important to be real with yourself at what you're good at. No one wants to admit they're not good at things, but I think it's really important because you're going to make a better product and a better team. Hey, you know what? I don't have the technical stuff or I'm not the best, um, at talking to people. So I need someone to help, uh, fundraise and someone who's going to be really good at raising money and I'm going to be the product guy because I'm really good at marketing and I'm really good at product. So I think you really want to just be real with yourself on what you're good at and what you're not so good at.

Speaker A: One thing as we, uh, uh, our time draws, uh, to a close is I always want to ask people at the end of a podcast, uh, this has become a makeshift CMO tradition is if I gave you 10 million bucks, well, you could fail. But in your mind if you had 10 million bucks, you were probably thinking, I can't fail, uh, to start any company. Um, let's say you're done with Rent Sync. You guys have a great exit. Someone comes along and says, josh, you're awesome. I'm going to give you 10m million bucks. What do you do?

Speaker B: So part of me would say I'd buy some real estate. I think that we're heading into a high, uh, inflation, uh, like interest rates are rising, which typically brings down public, uh, market stocks. Uh, so I think public market stocks are not going to be great over the next three to five years. So you want cash on cash businesses. So apartment buildings are typically good in that. I know the industry, I'd kill it on the marketing side. So the easy answer would Be I'd buy some real estate and run that and be the marketer. But that's not really the fun answer. Uh, I actually think a business I would start is I would actually create. It's a very unsexy answer, but accounting software for Hollywood studios. Um, my brother.

Speaker A: Really?

Speaker B: Yeah, my brother works in the industry, as does my aunt actually and my uncle. Uh, so I have a couple people that work on the uh, on the finance sides in uh, Hollywood. And, and they all tell me how antiquated the uh, software is. And I can tell you also from just internal processes that we change softwares on our end. And yes, there are softwares out there to help improve accounting, but there's still industry specific needs. And so we've switched softwares a couple times just to say, hey, what works best for our specific needs. This goes back to the customization and you know how many CRMs out there? There's thousands. Uh, Salesforce is a very good generalized CRM, as is HubSpot. But there are sales. There uh, are CRMs out there for daycares and schools and nurseries and camps. And it's very specific to uh, uh, niche. And I think that that could be the true as well in the world of um, accounting. And I think that Hollywood studios, big business, and I know they have a lot of very specific needs. Again, I'm not the expert there, um, but I've spoken to my brother at length about this. Uh, and so, yeah, I think that's an area that again, it's unsexy. But this is the other thing I think that sometimes people need, uh, to realize is there's a lot of money in unsexy industries. Uh, you know, growing up, everyone wants to be an athlete or an actor. Uh, today I guess you'd call it a content creator or something. Uh, those are super competitive industries because everyone's in there. No one wants to get into, uh, hey, we're going to do, um, tire recycling or something like that that no one cares about, um, or scrap metal. These, these industries that actually have very high cash yields, they're unsexy. No one wants to be in them. Um, and so typically they're, they're kind of ignored. Um, but I think that there's a lot of money to be made in there. Actually, one of my favorite businesses out there is Flexport. I don't know if you know it. It's a logistics company. It's a.

Speaker A: Yes. Yeah, logistics.

Speaker B: Logistics isn't sexy. It's come into foray ever since COVID because You know, there were lockdowns and supply chain issues. And so people have now thought of it much more. But those are industries that can really grow are these unsexy industries that people don't think about. And so I really try to think about them. And the last thing I'll say on this idea of, like, what business would you think of? I used to always have this exercise with my buddy because he always said, oh, I want to start my own business. I said, what do you have? He said, I don't have the perfect idea. So I always say, you're never going to get the perfect idea. But do this for me. Write down 100 ideas. Said, how am I going to come up with 100 good ideas? I said, you're not going to come up with 100 good ideas. But if you come up with 100 ideas for a business, 90 of them are going to be really bad. Honestly, they're going to be terrible. And then another five of them are going to be okay. Three are going to be good, and maybe one or two are going to be great. And that's really it to me. If you really want to find a great business, the first, uh, idea that pops in your head is rarely going to be great. But come up with 50, 100 ideas, and eventually you're going to find a great idea. And again, it's really about finding where there's a disconnect, where people are wasting too much time or there's just not enough value being added. So I really try and find that. And so sometimes in my own life, I say, hey, this is really annoying. How could I improve that experience and think about that as a business? Uh, but again, that's really where I try to look is in the unsexy areas.

Speaker A: That's awesome. That's a really good way to put it. And, uh, for those out there, uh, who are, uh, who have that bug inside them, they're like, I just need to quit my job and they start a business. Uh, that's a great tip for you. Write down a hundred ideas. Uh, because, uh, the reality is 90% of them are, are going to be bad. And as an entrepreneur, you're probably going to hear that 90% of your ideas are bad. So you better get used to the fact that people are going to tell your ideas suck, because that's the price it takes to be an intrapreneur entrepreneur, whatever it is.

Speaker B: Um, yeah. And don't be afraid to pivot. You know, I think too many people, um, you know, again, I'm data Driven, um, if you think something's true, well, just don't care. Don't be afraid to change and go where the data falls. That's a big thing. I try and tell everyone at uh, work I try to instill in my team is sometimes we think something. I often make product changes to uh, the uh, and I think one thing's going to happen. I'm a big believer and you know, I say this is what I think is going to happen when we make this product change and it doesn't happen. So you have to test your theories. You can't just go on your gut, uh, again, your gut can lead you, but you have to back this up. And so don't be afraid to follow the data. And we have found sometimes some interesting things where we've said, oh, wow, this, we didn't expect this, let's keep looking into that further. And we found some amazing product innovations just by following the data that have led to higher customer retention, um, or just more leads for users. And so really, uh, don't be afraid to change your mind based on what the data says.

Speaker A: That's awesome. Um, because this is a marketing focus, uh, podcast towards founders and early stage teams. I gotta do something cheesy at the end. What's your call to action? Josh, you gave us damn near an hour of your time. Uh, the least we could do is let you plug something in the show notes something that you're passionate about, whether it's a cause or yourself.

Speaker B: Sure. When you said call to action, I thought you meant imagine there's a, there's a billboard that says Josh, what's your, what's your slogan? Or something like that.

Speaker A: Actually, hey, you could, you could say

Speaker B: that, um, you could say that this is my slide. Slack by in on Slack, it says, you know, what do you do? And you're supposed to write your job, but I just write get shit gets shit done. That's really my motto in life and at work especially is you just got to find a way. You know, sometimes it's going to be messy, sometimes it's going to be ugly. Uh, but especially in the startup world, like things aren't going to be perfect and I'd rather have a really good product 85% of the way there today than a perfect product in two years. You know, it's, it's never going to be perfect, but you got to put it out in the world and see how it works and again, get that real world data and see how people react to it. So that's my personal, uh, slogan. As for where you can find me, if you'd like, you can connect to me on LinkedIn. Joshua uh, Lipton. I, um, don't really have too much else. I actually keep a low profile on social. Um, most of my things are private. Um, but yeah, so I'm not going to call anything out. Though I will say if you are looking, we are always looking for smart, hard working people at rensync. So if you are a smart, hard working marketer, which I'm sure all your listeners are, uh, you know, connect with me on LinkedIn and uh, if we have some jobs available, which I think we do, coming down the pipeline, uh, we're always looking for those kinds of people. So yeah, we'd love to connect.

Speaker A: Josh, thank you so much, uh, for joining us and uh, the Makeshift CMO. Really enjoyed having you. Thank you so much.

Speaker B: Been a pleasure. Thanks Bruce.

Speaker A: Thanks for listening to this edition of the Makeshift cmo. If you want to follow what we're doing to help early stage startups, founders and marketers, subscribe on Spotify, Apple or wherever you get your podcasts.

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