March 8, 2020

JF2014: Digital Media Tips With Shoshana Winter


Shoshana is a digital media veteran with 30 years of marking management experience on both the agency and client-side. She ran marketing for audible for 4 years before they were purchased by Amazon. She has the skills to help early-stage business’s grow through marketing. In this episode, she gives some great insight on how to think like a marketer when it comes to growing your audience base, whether that is listeners, investors, or distressed properties. 

Shoshana Winter Real Estate Background:

  • Digital media veteran, bringing nearly 30 years of marketing management experience on both the agency and client side
  • Now working at iintoo, the company has managed and raised 357 deals and $600M with a gross asset value of $2.5B
  • Based in NYC, NY
  • Say hi to her at

Best Ever Tweet:

“I think it’s not just about being lazy, I think we become lazy because we lost faith perhaps.” – Soshana Winter


Joe Fairless: Best Ever listeners, how are you doing? Welcome to the best real estate investing advice ever show. I’m Joe Fairless, and this is the world’s longest-running daily real estate investing podcast, where we only talk about the best advice ever,  we don’t get into any of that fluffy stuff. With us today, Shoshana Winter. How are you doing, Shoshana?

Shoshana Winter: I’m doing great, thank you.

Joe Fairless: Well, I’m glad to hear that, and looking forward to our conversation. A little bit about Shoshana – she’s a digital media veteran, bringing nearly 30 years of marketing management experience on both the agency and client side. Now working at iintoo. The company has managed and raised 357 deals, 600 million, with a gross value of 2.5 billion. Based in New York City, New York.

With that being said, do you wanna give the Best Ever listeners a little bit more about your background and your current focus?

Shoshana Winter: Sure. Well, you did a pretty good job of it. I come from an advertising marketing and media background. I’ve worked for many different large advertising agencies, and then spent a lot of time in senior marketing roles in digital startups. Probably the one that you guys are being most familiar with is Audible. I ran marketing for Audible for four years before Amazon purchased the company, so I’m very familiar with how to build audiences for early-stage companies using the internet as a tool

About two years ago I had the pleasure of meeting the CEO of iintoo, which was a relatively early-stage company in the online real estate investment space, at the time based in Israel. He was just about opening a U.S. office, because ultimately the real opportunity for real estate investments is in this market. I worked with the company for a while as a consultant, and then got asked to lead the company as a managing director of the U.S. headquarters about a year ago.

So I am new to the real estate space… Drinking from the fire hose would be an understatement of what I’ve experienced over the last 24 months… But what’s interesting is that I think a lot of my background, both working with early-stage companies, as well as understanding how to communicate and market directly to accredited investors is something that’s really coming in handy as we lead and grow this business in the U.S.

Joe Fairless: So your target audience would be accredited investors, it sounds like, yes?

Shoshana Winter: At the moment, the offering is just to accredited investors. As we look at the space evolving – and we plan to be here for a very long time – we are well aware of and interested in expanding that audience through different kinds of offerings. But in the short time we’ve been here in the U.S. market, that’s our focus right now.

Joe Fairless: I think a lot of people are gonna enjoy this conversation, because you have the deep experience in digital media and marketing in a way that isn’t typically brought to real estate investing and our industry… So what are some of the things that you all have done to reach accredited investors that have been effective?

Shoshana Winter: You said a couple things that I think are really relevant… I think that as much as — and I’m sure your audience is already pretty knowledgeable and excited about the real estate investing space… But I think that when you look at the U.S. investor audience more generally speaking, we’re a pretty conservative bunch, and in general we’re pretty passive when it comes to the way we both invest and sort of even think about portfolio diversification, for example.

So if you look at the big institutional players and the way we normally interact with companies where we have our IRA, or 401K, we pretty much either give it over to our financial advisor, or tend to invest in pretty traditional asset classes. So a lot of what we’re focused on is using digital communication – and I would say also traditional communication. This conversation, in many ways, is another form of audio or radio, that’s gotten much more popular… So we’re open to channels that work and that reach the right people at the right time.

But I think that ultimately, what we’re finding is working is understanding the American investor, what he or she is either knowledgeable or not knowledgeable about, and really being able to leverage digital channels, whether it’s search engine marketing, or doing partnerships with financial services, publishers like Forbes or Fast Company, to be able to tell our story in a way that really communicates the fact that this is a relatively easy, direct access way to get in on an asset class that traditionally had not been at our disposal.

So from a messaging perspective, we’re all about “This is easy, this is fast, you can do it on your own time. You don’t need to go through a financial advisor or a broker”, and the returns are, in many cases, higher than what the stock market and other traditional asset classes that are correlated to the stock market have been able to deliver.

So that’s sort of my long-winded answer to your question…

Joe Fairless: Yeah, that’s really helpful… When you think about it, it sounds like you think about it as 1) first understanding who you’re talking to, and from what you’re saying, the U.S. investor audience is pretty passive… Another word for it is “lazy”.

Shoshana Winter: [laughs] I didn’t wanna say that.

Joe Fairless: Yeah, I get it. It’s crazy to me, because the majority of people work so darn hard for their money, but then once they have the money, they don’t put some effort into growing that money so that they don’t have to work so darn hard continually. It’s a flawed logic, but that’s just how it is, and good luck changing that. So what you focus on – it sounds like it’s more about the category versus the product…

Shoshana Winter: Yeah, I think it’s both… Listen, anyone that’s in this space, or even in the investment space more broadly speaking, obviously knowing your audience really matters, because that’s going to drive where you talk to them, how you talk to them, and what you say. In their defense – just to speak to the “lazy” comment, which I completely agree with – I think it’s not just about lazy; I think we’ve become lazy because we’ve lost faith, perhaps…

In my own lifetime as an adult or working adult I’ve seen three major disruptions in the market that have affected my portfolio. There’s a book that was written about this called “Rational Exuberance”, which is although we look out the window today and in New York City it’s a beautiful fall day, with the sun shining, and the economy seems to be good shape, we’re always waiting for the [unintelligible [00:07:43].01] 2008 is not that long ago for a lot of us… So I think part of the passivity comes from a lack of transparency and understanding of what drives the market and how people’s individual portfolios are affected by things that they feel like they don’t have very much to do with.

And the beauty of real estate and what we really try to lean into is demonstrating to this target audience that actually this is a really transparent asset class. You can actually look at it and see it. It’s something that we’ve all experienced, because we live in homes and we go to work in buildings. This is something very organic and natural. And the way in which we choose to make those opportunities accessible is using that same kind of transparency.

So I think that it’s a marriage between understanding the audiences, the barriers to entry, the fear that they may have, or the lack of education, but I think more importantly, leaning into those trigger points that really help them change the conversation about what this could be.

I think the internet, even in the last 5-10 years, has demonstrated that if you do a good enough job at it from a product and experience perspective, people will begin to behave very differently. Look at the way we now think about booking a hotel room; going to Airbnb us now, the first thing people do. That was something that we wouldn’t have even thought about ten years ago.

So I think that we’re both part of an emerging group of companies that are trying to give traditional investors access to an untraditional asset class, but at the same time we’re also part of an internet revolution that’s giving consumers direct access to things they never had before, with better results… And those are the kinds of value propositions that we try to really leverage as we build the business.

Joe Fairless: Hypothetical scenario –  your marketing budget has been slashed in half (*gasp*) and you are only going to focus on one type of advertising. Where do you put that money?

Shoshana Winter: Any direct response marketer or direct marketer worth their salt (as they say) would probably say “Stick to what you know and what you know works.” So ultimately, as you yourself are a perfect example of this – this is a podcast that’s about a very particular subject… The marketing that really is most effective is one where a consumer self-identifies as being interested. So search is a great example of that. By the action of someone typing in “investing in commercial real estate” into Google, they are raising their hand and saying “This is something I’m interested in”, so therefore my ability to be able to capture their imagination and hopefully get them to visit my site and join is a lot more probably than, for example, if I decided to do a big billboard campaign all over New York City.

We know a lot now, we have a database of over 200,000 accredited investors, and the data that we use on a regular basis is not only to communicate directly with them, but to extract out demographic and psychographic information that we could then use when we go out and we buy a search campaign, or use social media. We’re able to create lookalike audiences based on all that data, so that we can really cut out the guesswork, if you will, around marketing and advertising, and only talk to those people that we have a shot at really converting from an interest level.

Obviously, as the category grows and this becomes (let’s call it) a less alternative way of behaving, I think that when you think about things like “I’ll advertise on television, or radio” – those things become much more interesting, because we already have a base of users that are pretty familiar with how this works, and are [unintelligible [00:11:48].14].

Joe Fairless: What are some demographic and psychographic information that you pull from your current database to create a lookalike audience to attract via digital ads?

Shoshana Winter: I’m so glad you asked about both, because I think in the data and marketing we tend to focus more on demographics. Obviously, because at the moment we’re going after a relatively small group of people in the United States – somewhere between 13 and 15 million accredited investors – because associated households’ income and personal wealth, they tend to be older and living in cities that are business hubs, versus rural areas, and they tend to be of a higher educational background. So all of those leavers, which I think are pretty obvious – and Fidelity is going after those people, and Schwab is going after those people – those demographics are pretty obvious. So obviously we take advantage of that. I think geography is an interesting one… What states or cities are there high concentration of accredited investors etc.

The second piece I think is where it gets really interesting… Which is to me, as a marketer and a business person, this is not just about how old you are and where you live. This is about an attitude. Somebody who’s going to feel comfortable after seeing an ad on Google, or on Instagram, to come through and either call us or sign up to create an account at iintoo, and then talk to a registered salesperson about the latest offering we have in Little Rock, Arkansas.

That person is probably a little bit more of a progressive thinker. He/she was probably an early adopter of other disruptive products, like Airbnb or Uber or Casper mattresses, or Warby Parker glasses. These are people who, despite their age – and I think the world likes to make us all feel very old and out of touch with technology… The truth is we have the most disposable income, and a lot of us are very much leveraging those kind of disruptive technologies to get more done in a day, to have more access and transparency to those things, and to do it in a way that feels personal to us.

So when we look at a progressive mindset, we look at things like “What are the other sites or services that these individuals are using on a regular basis? What are they reading? What products are they purchasing?” Those are the kinds of datasets that allow us to really think about our investor not as a number, but as a human being with a particular personality and a particular attitude when it comes to trying things like this.

Joe Fairless: And how do you determine what other sites are they on and what other products are they purchasing, what are they reading?

Shoshana Winter: Some may find this creepy, but the one thing that marketers and businesses have at their disposal today more than ever before is an incredible amount of data. I think a lot of us maybe speak about privacy, and issues like that, but at the end of the day, with the data that’s available to us, whether it’s buying a campaign on Facebook, or Google, and Amazon is becoming a bigger player here as well – those platforms, because of their scale, collect an enormous amount of data from their users. Where a user has visited before they came to the site; what are the groups that they’re members of if it’s a social site, for example…

These are old datasets, that although they’re never delivered to us in an Excel spreadsheet, they are used to create audiences based on certain kinds of attitudes or behaviors.

For example, let’s talk about the busy working mother; that would be an example of that. We’re able to take a group like that and go to a lot of our digital partners and provide them with the data we have – anonymized, of course – and say “These are the kinds of people that we’ve been very successful with. Can you find them on Facebook or Instagram?”

What most of these platforms are able to do because of the amount of data that they hold and use is to be able to identify those people within their own platform and allow us to target them with our advertising in a very precise way.

Joe Fairless: For someone who is listening and wants to learn from this process and do it, how do you do that exactly? If they have a list of people, like “You know what – I’d love to know more of what they’re reading, and what they’re purchasing… I have this database of people”, what are the steps that they would take in order to better target them and get that information?

Shoshana Winter: I’m gonna be honest about not being able to go through every step, because it’s not something that I personally do on a day-to-day basis…

Joe Fairless: Fair enough.

Shoshana Winter: I have a director of marketing and we work with a digital media agency… But even if someone had a relatively small business and they reached out to Google and said “I wanna do a campaign that reaches a particular audience. Here’s what I know about my audience”, the ad rep on the other side should be able to in some way, shape or form either extract the core parts of the data that the advertiser owns, without names, obviously, and/or replicate the demographic make-up on their own platform, and then allow them to create campaigns that are highly targeted to those groups.

Joe Fairless: Got it.

Shoshana Winter: It’s an art and a science in and of itself, and I don’t want at all to position myself as an expert, but I’m well enough versed in understanding how it works at a high level to know that where digital is really going and where marketers in this space and really in any category – the biggest asset they have is knowing who they’re talking to with as much granularity as possible, so that they’re not wasting their ad dollars on those individuals that are probably not going to be interested in being a customer.

Joe Fairless: It makes sense. On the flipside, what’s something that you all have spent money on marketing-wise, and you’re not doing that anymore, because that just was not a good ROI.

Shoshana Winter: That’s a great question. I think everything is all about timing. I mentioned earlier television and doing content on whether it’s Barron’s, or Fast Company, or in the world of financial services publications like the Wall Street Journal, where we know a large chunk of our audience probably is.

I think that the problem for a more early-stage marketer like us, or even let’s say somebody who’s starting their own business, is that those channels tend to be more expensive, and the impact that they have directly is sometimes harder to measure immediately. What you’re really doing – as we say  in the marketing biz – is more top-of-the-funnel: brand awareness, creating an immediate connection with somebody, but it might not result in an action.  So that’s not something we’re really investing heavily right now as we build the business, because really what’s gonna make it work at this stage is, as they say, getting to the low-hanging fruit. Those individuals that maybe have already expressed  an interest in this category.

Our company about six months ago made an acquisition of a competitive company in the space that had gone out of business, and with it we were able to inherit assets to their database of accredited investors. That in many ways was a piece of marketing. It was our ability to be able to have a larger addressable audience of investors that have already raised their hand and said “I’m interested in commercial real estate.”

I think that as we grow and we exhaust the low-hanging fruit  and we wanna start talking to maybe more of the mom-and-pop investor, who maybe is more conservative, or maybe is not as progressive, but who we know can really benefit from it, from a portfolio management perspective, then we would start to look to things that are perhaps a little bit more expensive and not as direct, but help us to really tell a story in a more compelling way and build interest over time.

So I think it depends on what stage you’re at. I think almost anything can work, but I think it has to be at the right time and with the right measurement.

Joe Fairless: Yeah. Thank you for that information. Lots of great information. Just so I’m clear on one thing that you’ve spent money on that hasn’t worked – what is that one thing?

Shoshana Winter: I would say  right now to do a big TV campaign would probably not be the best use of my marketing dollars, just from a pure return perspective. I do think there will be a time, hopefully in the near future, where that will make sense for us… But right now that’s not something we would consider.

Joe Fairless: Got it. So you’ve been strictly digital since you’ve been on board in this capacity, for the last 24 months.

Shoshana Winter: Yeah, I would say digital and content, where content can have a life outside of digital, but I would say those are our two main focuses… And then we do spend a tremendous amount of effort in what they call CRM (customer relationship management). So marketing directly to our own base of users, some of whom have already invested and some of whom have not… And really trying to get to know them and offer them – whether it’s access to webinars, or eBooks, articles that we create, that will help make them feel more competent and informed about the category, so the notion of investing becomes a little bit more accessible.

Joe Fairless: And how do you get to know your own database a little bit more, tactically speaking? How do you execute on that?

Shoshana Winter: I think a combination of email, as old as it is, is a very powerful medium. It allows you to create tiny little audiences based on how active somebody is, because we have all of that information. Audiences based on things like “Have they invested in the last six months? Have they not? Do they tend to invest in deals that are in certain geographies or not?” So what I think email marketing allows us to do is get very sophisticated about how we segment the audience, and then create really customized content or messaging, that we believe is going to work best with that audience, versus just sending out a lot of mass mail, if you will.

So email has been very powerful for us, both in terms of segmentation and then in terms of the data that we get back after an email is sent. What was the open rate, what was the click-through rate, what are people doing as a result of said email? That’s one, I think.

And then the other may sound kind of old-fashioned, but we’re an investment company, and at the end of the day this is about building a relationship between a registered investment professional that we have on our team, that will pick up the phone, welcome members to the platform, and through conversations over time enable them to feel comfortable enough and informed enough about a particular opportunity. And we keep all of the data that gets collected by the salespeople on an internal, proprietary platform that we have, so you can go into our platform as a salesperson and look up an individual investor and really get a full history of what he/she has/hasn’t done over the life of their membership at iintoo, which is incredibly valuable when we’re having a phone conversation or sending out emails.

Joe Fairless: What CRM platform do you all use?

Shoshana Winter: We’re using HubSpot as our marketing automation platform, and then some of our CRM is actually built on top of our portal, so it’s a combination of the two.

Joe Fairless: Anything else as it relates to this topic that you think we should talk about, that we haven’t talked about, before we wrap up?

Shoshana Winter: I think that those of us in the online real estate investment space – these are early days in a category that I think is really gonna change the way people think about their money. And I think it’s an exciting time to really be on both sides of it – as an investor, and on our side, as a business that’s trying to communicate and get that investor to invest a portion of their portfolio with them.

I think it’s just really incredible that regular retail investors that don’t know somebody in the business and don’t have to put in a million dollars can invest into a deal and see double-digit returns in a short period of time… So I just think it’s an exciting time to be in this space, to be marketing in this space and to be an investor.

Joe Fairless: I loved our conversation. Lots of really good tips for how to think about marketing to accredited investors, and specifically how to reach them. Some challenges, as well as some solutions. Shoshana, how can the Best Ever listeners learn more about your company?

Shoshana Winter: The website is pretty easy to follow, and there’s an email address on every single page,, which gets answered personally every single day. Or you could just pick up the phone and call us, and we’ll talk to you.

Joe Fairless: Thank you so much for being on the show. I hope you have a best ever day, and we’ll talk to you again soon.

Shoshana Winter: You got it. Thank you so much.

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