Capital Gains -

How do you go from comfortable affluence to real wealth? Listen to the Capital Gains podcast, by, with host and professional real estate investor Jonathan Twombly. In interviews with top professionals, we'll discuss alternative investments you might not have known about that can help you go beyond merely obtaining a passive income to growing your asset base and becoming truly wealthy.
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Apr 25, 2017

Whenever an artist, like a musician, creates a work, they create a valuable asset with an income stream called a royalty. Royalties can be bought and sold, and are a unique investment.

If artists want to convert the unrealized value of their royalty stream into present cash, they can sell it on Royalty Exchange, an online marketplace for buying and selling royalties. And today's guest is Jeffrey Schneider, president of Royalty Exchange.  

Investors have discovered what great assets royalty producing intellectual property like music can be. And they come to Royalty Exchange to buy those assets.

Listen to the full episode on for details on how investors purchase royalties from artists and the benefits of these investments, as well as the different types of assets available.

Apr 4, 2017

Today's guest is Nicholas Coriano, who can only be described as a true self-made man.

Nicholas owns Homescape LLC, a holding company for his various investment interests. Which include domain names, and eCommerce development, coins and precious medals, and raw land. Nicholas truly embodies the audience of the Capital Gains podcast.

Tune in each Tuesday for a new episode of the Capital Gains podcast, presented by

Mar 28, 2017

Now, I'm willing to bet that you didn't realize that a lawsuit is an asset for the plaintiff. If the case is very strong, it's a very valuable asset.

Since the 1980s, people have been investing in lawsuits by advancing the cost to the plaintiff in return for an agreed portion of the award or settlement.

Today's guest is Jay Greenberg, co-founder of LexShares, which funds litigation.

Before he co-founded LexShares, Greenberg worked in Deutsche Bank's tech investment banking group. There, Greenberg focused on merger and acquisition advisory, debt and equity financing (primarily for enterprise software), tech services, and fintech companies.

Subscribe to our podcast on iTunes and read more about the Capital Gains podcast on

Mar 21, 2017

Welcome to the Capital Gains podcast! I'm your host, Jonathan Twombly.

Today's guest is Scott Meyers, the owner of Self Storage Investing.

Scott has an amazing story having worked his way up from buying $30,000 houses to bigger multi-family deals and then into self storage. Scott is now one of the countries leading experts on self storage investments, with a portfolio of more than 4,000 units around the country.

Tune in to this great episode and more at!

Mar 8, 2017

In this episode of the Capital Gains podcast, Jim Bronstein of Marine Business Advisors shares why investing in marinas and boat yards could be worth your while.

Jim has been in the boat yard and marina business for more than 35 years as an operator, investor, consultant and investment advisor.

On today's show, he tells us how the marina business has grown from a mom and pop hobbyist endeavor to a serious investment asset that's highly sought after by real estate investors and private equity firms alike.

If you're interested in how to invest in marinas, there's no one better to know than Jim Bronstein.

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Mar 8, 2017

Welcome to the Capital Gains podcast with Jonathan Twombly. Today's guest is Christie Pitts, a venture development manager at Verizon Ventures.

Christie talks about corporate venture capital and how it differs from traditional venture capital.

In particular, she explains, corporations seek to invest in early-stage companies were the deal not only makes sense from a financial perspective but the target company is a strategic fit with the corporation's overall business interests.

Listen to the Capital Gains podcast each week at

Feb 28, 2017

Today's guest is Steve Waldman, president of Ground Lease Capital Partners.

Now, if you're not into real estate, I'm willing to bet that you never knew you could buy a piece of land without buying the building on top of it, and then give the building owner a lease allowing the building to be on the land.

Well, it's called a ground lease, and Steve Waldman has made a career out of them, helping building owners increase their returns by stripping the land piece from the property and helping his own investors make returns by owning that land.

In this interview, Steve walks through the process of exactly how you make money doing this kind of ground lease deal.

Feb 3, 2017

Today’s guest is Angela Lee. Angela teaches leadership and strategy and entrepreneurship at the Columbia Business School here in New York City. She's also the founder of 37 Angels, an angel investing network that trains women to invest in technology startups.

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Feb 3, 2017

With more than 30 years in the metals business, Peter Hug, Kitco's head of precious metals trading, has seen everything from the Hunt brothers' attempts to corner the silver market in the 1970s, to the great bull run for gold after the 2008 financial crisis, to the steep drop in prices that followed. Tune in to this episode to learn about investing in precious metals and catch more Capital Gains at

Feb 3, 2017

Today's guest is Justin Cooke, co-founder of Empire Flippers, a marketplace for buyers and sellers of operating online businesses.

Online businesses, from simple informational pages creating revenue with Google ads, to more sophisticated platforms selling physical products through Amazon, have hit the radar screen for investors.

From small investors looking to buy a job running an established web business, to website flippers who create value by massively increasing traffic and conversions, to private equity funds looking for new asset classes with strong yields, many people are now looking at existing online businesses as the next great investment category.

Tune in to this episode to hear Justin Cooke explain why, and find more episodes at

Feb 3, 2017

In today's episode, Team Valor International owner Barry Irwin talks about racehorse ownership, how investors can make and lose big money investing in thoroughbreds and how smart investors invest in racehorses the same way venture capitalists invest in startups.

One things clear from this interview: investing in racehorses isn't child's play. Learn more about investing by subscribing to the Capital Gains podcast and visit

Jan 18, 2017

Today’s guest is Mark Podolsky, the original land geek himself. In this episode Mark Explains how he set himself free from a hated investment banking career by learning how to buy and sell raw land. Mark is now the country’s leading expert on how to buy raw land for pennies on the dollar, sell it fast and make profits of 300, 500, and even 1,000% in just a few weeks. Best of all Mark does it from the comfort of his own home working only a few hours a week. 

Learn more about the Capital Gains podcast at

Jan 18, 2017

Today's guest is Joe Stampone, an expert in real estate investments, a partner at Atlas Real Estate Partners here in New York City, and the original student of the real estate game.

In this interview, Joe and I go deep into why real estate should not be considered a passive investment, the only way we know how to make it passive and why investing in apartments beats investing in single family homes every time.

Find more episodes of the Capital Gains podcast on

Dec 15, 2016

Investment diversification is an important topic for any serious investor, mainly because you don’t want to have all of your investment eggs in the same types of baskets. That’s where alternative funds come in. An alternative investment is an asset that is not one of the conventional investment types, such as stocks, bonds, or cash. For that reason, it’s not an area of investing typical investors are familiar with, which is why I invited Sang Lee to come on the show. Sang is with DarcMatter, an online platform that deals almost exclusively with alternative investment assets, making them available to any accredited investor. On this episode of Capital Gains, you’re going to learn why alternative investments are a smart move when it comes to investment diversification and how the DarcMatter platform works.

Are your investments diversified enough to be safe in a downturn?

Most investors understand the need to have their assets and investments diversified. When risk is spread out over a number of sources your assets are less vulnerable to market changes and fluctuations. But most investors are not aware that with the digital age there are new opportunities for investment that were previously unavailable to average investors. That’s where DarcMatter comes in. It’s an online investment platform that focuses on alternative investments. On this episode, I spoke with Sang Lee, CEO and Founder of DarcMatter about how the platform makes uncommon investments a reality for average investors. You’ll be intrigued by how the platform works and what it has to offer.

If you want to diversify your investment base, there’s a new way to do it.

The traditional investment portfolio doesn’t usually include much in the way of international assets, but online platforms like DarcMatter are changing all of that. In your DarcMatter account, you can diversify your investor base by accessing both domestic and international LPs. But you won’t be doing it in the dark. You’ll also be able to streamline your investor interactions and track all communications through the dashboard. And you don’t have to worry about compliance issues either. DarcMatter’s system has you covered, ensuring that everything is done above board. You can find out more about the platform by listening to this conversation I had with Founder, Sang Lee.

You can now have direct access to alternative investments.

The digital age has brought many changes to the traditional business models of the past - Uber, Airbnb, and others are changing the landscape of the way we do business and procure services. The same is happening these days in the realm of investing. Companies like DarcMatter provide transparent access to pre-vetted hedge-fund managers, private equity funds, venture capital, and other group funds to help you take advantage of opportunities that may have seemed out of reach before. Sung Lee, CEO and Founder of DarcMatter is my guest on this episode of Capital Gains.

Now it’s easy to find vetted alternative investment opportunities.

When you login to the DarcMatter interface you’re able to browse investment opportunities using built-in search features that allow you to drill down into the exact areas and niches you are interested in pursuing. And the system keeps in mind how you’ve completed your investor profile, suggesting funds based on your personal or client risk profiles and investment preferences. It’s a tailor-made alternative that you’re able to do online, on your own. You can directly indicate your interest in a particular fund, allocating as you please. You’ve got to find out more about this amazing platform and the investment diversification that’s possible using its powerful features. Find out how Sang Lee and his team have designed DarcMatter to be both effective and easy to use, on this episode of Capital Gains.

Outline of This Episode

  • [1:01] My introduction to Sang Lee of Dark Matter.
  • [1:28] The industry of alternative funding and how Dark Matter fits in.
  • [4:21] Who are the end users of Sung’s company?
  • [7:51] Why many advisors are leaving institutions these days.
  • [8:54] How funds become part of this particular investment platform.
  • [11:16] What an investor might walk through to use the platform.
  • [13:42] The investment minimums on the platform.
  • [17:05] How Sung began his company.
  • [20:00] How DarcMatter changes the game for investors and funds.
  • [23:43] The trajectory the company has been on and where it’s headed.
  • [26:15] What investors can expect the first time they login to DarcMatter.
  • [28:13] Forecasting the next 5 to 10 years for DarcMatter.
  • [29:43] Why alternative funds are an exciting area for growth opportunities.

Resources & People Mentioned

Jonathan's Websites

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Website: On Youtube On Facebook On Twitter On LinkedIn

Dec 9, 2016

If you haven’t heard about Bitcoin, the first example of cryptocurrency, you’re not alone. Over 10,000 times per month people are Googling the question, “What is Bitcoin?” I’d heard about Bitcoin a number of times but still felt like I didn’t have enough of a handle on what it is and how it works, so I decided to invite an expert on the subject to talk with me for the podcast. On this episode, I chat with Trace Mayer, one of the leading experts on the Bitcoin phenomena. He’s not only going to tell us what Bitcoin is, but also how it works, why it’s becoming more and more popular as a form of currency, and how you can get in on the Bitcoin movement.

How can a currency be digital in the first place?

Everything we’ve ever known and used as a currency has been tangible, something we can hold in our hands. But Bitcoin is changing all of that. Now you can transfer value - money, as easily as you transfer a file to someone over email. Only it’s encrypted using the same industry leading standards that many banks and financial companies use so that the value is kept intact, safe from the eyes and hacks of crooks who might want to exploit or use it themselves. Every transaction is tracked. Ownership of every coin is known. And it’s gaining ground worldwide. Find out what Bitcoin is and how it works by listening to this conversation with Trace Mayer.

What is it that gives Bitcoin its value? What’s to keep techies from simply inventing more?

When I first began this conversation with Trace Mayer I was a bit skeptical about the Bitcoin technology. But the more I got into the topic with him the more I understood that my skepticism was based on the fact that I didn’t understand the technology enough. As Trace began to explain to me how Bitcoin was first invented and the safeguards that have been built into it to ensure that its value is inherent and can’t be lost, it all started to make sense to me. You can learn more about how the Bitcoin system works and why it’s thought to be the currency of the future, on this episode.

Could the government ever make Bitcoin difficult or illegal to use?

Much of the fear surrounding Bitcoin has to do with the fact that it’s a completely new way of doing things when it comes to exchanging value in a transaction. Nobody really knows what the United States government or any government for that matter will do in attempts to regulate it, modify its use legally, or restrict it altogether. My guest today, Trace Mayer thinks that any steps that governments take should be to support and encourage the use of digital currencies like Bitcoin because it’s a more secure and stable currency than any that has ever existed - and makes exchange across currencies even easier. You can hear Trace’s argument and learn how Bitcoin is growing in value almost daily, on this episode of Capital Gains.

What happens to Bitcoin of the electrical grid goes down?

One of the biggest areas of vulnerability for any digital asset (computers, smartphones, online systems of any kind, etc.) is its dependence on a functioning electrical grid. Should something happen to bring down the infrastructure of a nation, or the entire globe (think natural disaster or effective EMP attack) then Bitcoin would be impossible to transfer and use. When I asked Trace Mayer about this possibility he had a very interesting answer that I think will get your wheels spinning. You can hear what he has to say about it on this episode.

Outline of This Episode

  • [1:08] My introduction of Trace Mayer and the issue of Bitcoin as an investment.
  • [2:22] What is Bitcoin and how is it used?
  • [4:22] What is it that gives Bitcoin value?
  • [8:20] How Bitcoin value can be proved instantly by digital means.
  • [10:44] The limited supply of Bitcoins: How do we know it’s true?
  • [13:44] Can Bitcoin be gamed or compromised technologically?
  • [16:46] The risks to Bitcoin.
  • [18:34] Competitors to Bitcoin and why they don’t threaten Bitcoin’s value.
  • [21:00] The incredible advantages that being first gives.
  • [25:15] Could the government make Bitcoin difficult to use?
  • [27:53] Trace’s book and the premise of it.
  • [32:38] How could you get involved in the Bitcoin market?
  • [38:00] Trace’s beginning experience with Bitcoin.
  • [42:13] The risk of losing Bitcoin should the electrical grid go down.

Resources Mentioned

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Dec 6, 2016

Every investor wants a good return on his/her money. But is social impact something that you should be concerned about when it comes to where your funds are invested? For some years now certain individual investors have been concerned about the companies included in mutual funds, etc. for the sake of ensuring that they are not financing companies they are averse to supporting. But can it be done on a wider basis? Can social impact be a driving force behind not only a company but an investment fund? That’s exactly what we have in Bridges Ventures and today I’m talking with Brian Trelstad, partner of the firm to find out what Impact Investing is and how it’s becoming one of the more sought after ways of investing these days.

What IS an impact investment?

One of the basic questions I had to ask my guest today was this: What IS impact investing? Brian Trelstad is a partner at Bridges Ventures, an investment fund that aims specifically at investing in companies that are not only socially conscious but more so, are aimed at particular social issues that they want to address through the success and profits of the company. Those are the kinds of companies that are of great interest to Brian and the Bridges Ventures team because they are not only profitable and viable investment opportunities but are also making a difference in the world on a broader scale. Learn more about Impact Investing on this episode of Capital Gains.

Intentionality and accountability make the difference in Impact Investing.

When I asked Brian Trelstad what makes one recipient of a person’s funds a charity and another an Impact Investment he was quick to point out two things that define the difference: Intention and accountability. The Bridges Ventures team seeks out investment opportunities that are specifically aimed at a societal problem that the profits of the company are intentionally aimed at addressing. But they also look at the ways the company in question is aiming to support their favored cause and how they plan to be held accountable to do it. It's very different than charity giving. Find out more about the social impact of impact investing on this episode.

Is there a trade-off between a company having social impact and being profitable?

When you hear of a company like Tom’s Shoes that makes a huge investment in meeting the needs of people in specific areas of the world, do you ever wonder how much the profitability of the company is hurt because so much of their labor, materials, and shipping costs are spent producing products that will realize no profit at all? I asked my guest, Brian Trelstad if there is a trade-off between social impact and profitability and was pleasantly surprised at his answer. You can hear how he responded by listening to this episode.

Does an Impact Investment fund bring in the same type of returns traditional funds do?

Since this is a show about investing it seemed natural to me to get a feel for the rate of return socially conscious companies realize in comparison to companies that are not intentionally aimed at such causes. But I also wanted to know how an investment fund like Bridges Ventures - one that invests only in socially impactful companies - fares when compared to other more traditional investment funds. You’ll probably be surprised to hear the great rates of return the Bridges team sees through their investment philosophy. You may also be impressed with the extra levels of due diligence in which the Bridges team engages to ensure that every investment is as close to a guaranteed winner as it can be. Brian shares the Bridges Ventures approach to social impact and Impact Investing on this episode.

Outline of This Episode

  • [1:03] My introduction of Brian Trelstad, partner at Bridges Ventures.
  • [1:51] What does Bridges Ventures do and how does Impact investing work?
  • [5:24] What exactly IS Impact Investing?
  • [7:05] How does Impact Investing differ from charity?
  • [9:11] What’s the difference between an Impact Investment and an investment in a company that happens to be socially beneficial things?
  • [13:20] How Bridges Ventures evaluates a potential investment.
  • [16:32] What makes a business and its potential impactful enough to be funded?
  • [19:57] What Bridges Ventures brings to the table to help impactful businesses succeed.
  • [23:02] Is there a trade-off between philosophy and profitability?
  • [29:36] How do the financial returns of Bridges Ventures funds compare to others?
  • [35:15] What might make a real estate investment impactful?
  • [37:21] Concern for the people of the neighborhood when developments go in.
  • [39:30] Who Bridges Ventures investments are aimed at and how you can get involved.

Resources & People Mentioned

Nov 22, 2016

John Livesay is known as “The Pitch Whisperer.” He coaches startup founders who are seeking funding in how to best prepare their pitches to get maximum response. He knows the realm of pitching for funds inside and out, not just for the sake of getting money but also in terms of what investors are really looking for in startups and in their founders. If you are at all interested in learning how to be more effective in pitching your idea to investors, or are an investor who is looking to gain more knowledge about how to assess startups and their founders, this episode with John is going to be of great benefit to you.

Your idea may be good. But if you can’t effectively pitch it to investors it’s hopeless.

There are many product and business ideas that could probably make a significant impact on their target market and truly meet a legitimate need. But they never see the light of day because the people behind the idea are not good at packaging and presenting it to the people who could make it happen - investors. If you want your investment pitch to be the most persuasive and successful it can be, you need to know my guest on this episode, John Livesay. John generously shares a wealth of insight from his work with startup founders and investors to help you understand what goes into a great pitch and how you can become skilled at giving a pitch to investors. Be sure you listen.

Best practices for preparing your investment pitch.

Many founders or business owners try to pitch their idea to investors without the proper preparation - both of their idea and of themselves. John Livesay has developed a very specific process that walks startup founders through the stages of preparation that can make their pitch compelling and persuasive - but he also helps the person presenting the pitch craft the right stories, develop their personal mindset, and hone their speaking skills to make the presentation go off without a hitch. The number of founders he’s helped get their ideas funded is impressive. You’ll enjoy hearing his story on this episode of Capital Gains.

Why you need to pull investors in with stories instead of pushing them with information.

You may have some very compelling data or facts that show the veracity and need of your product or service. But if you can’t convey it in a way that shows that the idea will meet real needs and that YOU are the person to make the idea come to life, you will have a hard time convincing investors that it’s worth their time and money. John Livesay insists that every founder he leads through crafting their perfect pitch develop stories that draw the investors in. You can find out how he does it in this episode.

The best investment pitch advice: Ask for advice instead of money.

One of the things I asked John Livesay on this episode was how startup founders can best go about pitching their ideas to investors. He said the single most important thing is that the founder learns to ask for advice, not money. When you ask for money you’ll typically only receive advice. But when you ask for advice you’ll not only get a lot of questions and interest, you also open the door for the potential investor to learn more about your idea and get excited right alongside you. That often brings investment offers - which is what you want in the first place.

Outline of This Episode

  • [1:02] I’d like you to meet my guest today, John Livesay - the Pitch Whisperer.
  • [3:00] How John came to realize that startup founders needed help pitching their ideas.
  • [8:44] The types of startups John has worked with and what he’s looking for.
  • [9:30] The process John’s clients walk through - 8 online modules.
  • [11:12] How John vetts his clients.
  • [13:03] The types of things John’s clients learn in his process.
  • [16:49] Best practices for preparation for a pitch or presentation.
  • [18:10] What investors should be looking for in a potential investment opportunity.
  • [22:44] What is important when it comes to the value of the team and the value of the concept?
  • [23:24] How you can better prepare your pitch and identify potential investors.
  • [25:28] Why you need to pull people in with stories instead of pushing them with facts.

Resources & People Mentioned

Jonathan's Websites

Connect with


On Youtube

On Facebook

On Twitter

On LinkedIn

Nov 8, 2016

If you want to know how to become an angel investor you need to hear this conversation. I chat with Kathleen Murray, a businesswoman and angel investor who stepped into the world of angel investing on her own, supporting a startup company in the wine industry that she still works alongside today. Interestingly, she isn’t sure she would invest in the company again if she was starting over and you can hear her explanation in our conversation. Kathleen is a person who is very clear about the risks and rewards of angel investing and has a great way of describing the process, including how to get started as an angel. If you’re interested in the possibility of investing in startup companies, Kathleen has a helpful perspective on her own journey that can help you consider all the options, so be sure you listen.

Why would you NOT invest in a company you’ve already invested in, if you could do it over?

In this conversation with Kathleen Murray, an experienced angel investor, I learned how she got started in angel investing through a relationship with a company in the wine industry. In the course of our conversation she said that if she had it to do over again, she isn’t sure she would invest in the company in the first place. Why is that? It has to do with the long-term nature of the investment, the constant infusion of cash that’s been required to keep the company profitable, and the lack of a clear exit strategy for her investment. You can hear all the details on this episode of Capital Gains.

Are angel investments good for income or is all about the exit?

One of the things I was curious about when talking with Kathleen Murray was whether angel investments are typically income producing or if the profitability is typically realized at the end of the investment period. Kathleen was quick to point out that seldom is a startup company able to realize the kind of profits that enables investors to be remunerated in an ongoing manner. The funds that are put into the company are used to make it become profitable, not to enable quick profits - and there is a very clear difference. You can hear Kathleen’s clear and simple way of explaining the role of an angel investor on this episode.

Who should and should not get involved in angel investing?

If you’ve ever wondered whether or not angel investing is for you, my guest Kathleen Murray has some very clear questions she suggests you ask yourself to determine if angel investing is a good fit. Do you have extra income you don’t mind losing if a deal doesn’t work out? Are you excited about business and supporting new businesses? Are you eager to help new entrepreneurs who have great ideas? Are you willing and able to provide counsel, advice, and coaching? These are just some of the questions Kathleen shares so be sure you listen to get the entire list of things she says you should consider.

If you want to become an angel investor you need to go in with your eyes wide open.

Kathleen Murray says that angel investing is not for the faint of heart and not for those who want a passive investment. Angel investing requires a good deal of time - in the beginning stages it's spent going through a thorough due diligence process to ensure the investment is in your best interest, and once the investment is made, walking alongside the company founders helping them think through and navigate the challenges of starting a new business. Kathleen does a great job of outlining the commitment and time it takes to be a truly helpful angel investor on this episode.

Outline of This Episode

  • [1:02] My introduction of Kathleen Murray of The Executive Forum Angel Investment Group.
  • [2:10] How Kathleen got into angel investing in the first place - and her first experience investing in a startup company..
  • [5:00] The 3 main things Kathleen considers when checking out an investment opportunity.
  • [8:40] Are angel investments good for income or is it all about the exit?
  • [11:14] Who should and should not get involved in angel investing?
  • [14:08] How can an investor get involved in an angel investing group?
  • [16:23] How Kathleen founded The Executive Forum Angel Investing group.
  • [17:34] The types of Kathleen likes and doesn’t like.
  • [20:30] The reason Kathleen looks for companies to be addressing a real, lasting pain point.
  • [24:12] A disappointing experience Kathleen had that you can learn from.
  • [25:56] The importance of going in with your eyes wide open if you want to become an angel investor.
  • [27:45] What’s the difference between an angel investor and someone who invests money in a friend’s company?

Resources & People Mentioned

Nov 1, 2016

If you’ve heard the term “angel investor” but haven’t been sure exactly what it’s about, this is the conversation for you. On this episode, I chat with Jim Sullivan, an experienced businessman who has only been working as part of an angel investing group for just over two years at the time of our conversation. He’s the perfect guy to explain what angel investing is, how investing groups come together, how they assess potential investment partners, and what they are aiming to achieve in the end. I think you’ll really enjoy hearing Jim’s perspective on what it means to be an angel investor. He’s even got some advice on how to get started in angel investing, so be sure you make the time to listen. 

Why would an individual investor join an angel investing group?

Of course, anyone who has the money to invest in startup or first stage companies is able to do so. But doing so on your own can be very risky. An angel investing group is a partnership of individual angel investors who agree to work together to consider, assess, and advise early-stage startup companies in search of funding. The members of the group share the load of examining the risk VS reward of investing in the various companies and together make the decision to invest or not. It’s a great way to share the burden needed to make truly smart investing decisions. Jim Sullivan of The EF Angels investing group helps us understand how it works and is my guest today, on this episode of Capital Gains.

How does an angel investing group find its investment partners?

When you consider that there are always new companies looking for investment capital and that there are always investors who are looking to invest in promising new ideas and technologies, it may seem that getting those two parties together is a simple thing. But it’s really not. On this episode of the Capital Gains podcast, Jim Sullivan shares how he and his angel investment group make the first contact with potential startups through personal connections, introductions, and more. It’s proof that relationships and connections matter in business and you can hear how Jim and his group follow up with those first-time introductions to establish investment partnerships, so be sure you listen.

Why does an angel investing group perform “due diligence?”

Imagine someone you don’t know approaching you at the local coffee shop. The person tells you about his brand new company, the incredible ways he believes it will change a specific high-tech field, and asks if you have the funds to become an investor in what he’s doing. Would you be interested? Most investors wouldn’t simply because they don’t know enough about the person, his company and product, what stage of development and marketing he’s at, and is likely at least a bit ignorant about the market the product or service is targeting. In short, there’s been no  “due diligence” performed to ensure that the risk is one that is acceptable. Jim Sullivan is my guest on this episode and he explains what his angel investing group does in terms of due diligence so you can better understand how an angel investor makes decisions to invest or not invest.

The first things to consider if you want to be an angel investor.

When I asked my guest, Jim Sullivan what he recommends for the person who is intrigued by the idea of becoming an angel investor, he responded by saying that the first thing a person needs to consider is that they have a certain “risk threshold” - a level of risk beyond which they are unwilling to go. He recommends you know what your personal risk tolerance is and that you get your head around the idea that angel investing has no guarantees. You have to be prepared for the possibility that in every deal you may walk away with none of the money you’ve invested. It’s for this reason that Jim believes that angel investing is not for everyone and why he shares the kind of temperament that he believes is most suited to being an angel investor, on this episode.

Outline of This Episode

  • [0:41] My introduction of Jim Sullivan, angel investing, and more.
  • [1:03] Why Jim sees himself as a builder, investor, and operator.
  • [2:17] How Jim entered the angel investing field.
  • [5:44] The point at which Jim began investing his own funds in companies.
  • [7:21] How do deals come in to an angel investing group?
  • [9:31] The criteria Jim looks for in a potential angel candidate company.
  • [15:29] The next steps with an angel group.
  • [21:30] What does “due dilligence” mean within an angel investing group?
  • [27:27] What are good things for startups to spend their capital on?
  • [32:13] How to balance gut reactions from disciplined approaches.
  • [36:03] The different types of dilution in angel investing and their effects.
  • [41:00] What’s a disciplined approach to getting into angel investing?
  • [46:53] How you can connect with Jim.

Resources & People Mentioned

Jonathan's Websites

Connect with

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Oct 25, 2016

Creative real estate investing is not a typical concept you hear about. But Nav Athwal is not your typical tech founder. He has over a decade of experience in real estate as an attorney, broker, and investor. Nav lectures at UC Berkeley Law School and the Haas School of Business, is a frequent contributor to Forbes, and is often featured on CNBC, Bloomberg, and Fox Business. In this episode of the Capital Gains podcast, I talk with Nav about his online real estate investment platform RealtyShares. It’s created to bring investors and real estate companies together to make investments and funding seamless. We talk about how the platform was built and got started, how it works, and the kinds of people who best benefit from being a part of the platform.

Crowdfunding for real estate investment and funding? Yes. It’s true.

It was only a matter of time before the investment world - and in particular the real estate investment world - caught up with the way that technology and crowdfunding have changed so many other fundraising ventures. RealtyShares is an online platform that enables investors and real estate companies needing funding to come together to cooperate on vetted, verified deals that are poised to make money for everyone involved. On this episode, you can hear how Nav Athwal and his team have put the platform together and why Nav believes it’s on the cutting edge of the real estate investment strategies of the future.

Invest in real estate for as little as $5,000. Really.

Talk about creative real estate investing - this is it. When you sign up for a free account to become an investor with RealtyShares you are able to invest in amounts as low as $5,000 in projects or deals that have submitted all their details and financials - about the deal and the company overseeing it. Those companies are vetted and eventually approved by the experts at RealtyShares. It’s a great way to get started in real estate investing that is free of much of the risk that can happen in unverified deals. Nav Athwal shares how the RealtyShares platform is growing by leaps and bounds because of its simplicity and ease of use for investors, on this episode of The Capital Gains podcast.

RealtyShares is making it possible to get into real estate investing much sooner.

The average real estate investor has to work hard to save up a significant chunk of cash before he/she is able to get in on an investment deal. But Nav Athwal and the team at RealtyShares has made it possible for would-be investors to invest as little as $5,000. It’s possible through the platform’s ability to pool funds from a variety of investors to fund projects that exist within the RealtyShares database so that the real estate developer or company is able to get the funds they need from a variety of sources. The RealtyShares platform only earns 2% of the initial amount invested and the returns on the actual project are what provide the dividend to the investors. Find out more about how RealtyShares works on this episode.

Diversified real estate investing with only $5,000? Yes, it’s possible.

Because the RealtyShares platform combines the investments of many individuals or entities to fund development projects, they are able to spread out the funds of individual investors to mitigate risk. In other words, the money invested is used in more than one project. That makes the possibility of losing an entire investment smaller and the returns more likely. Of course, the RealtyShares team cannot and does not guarantee specific returns but the concept has built-in components like diversification that make it much safer for the average investor. RealtyShares is a great idea and is poised to change the real estate investing world forever. It’s truly creative real estate investing.

Outline of This Episode

  • [1:08] My introduction of Nav Athwal of RealtyShares.
  • [2:05] How investors and real estate companies are connected through RealtyShares.
  • [3:19] Nav’s background as engineer, attorney, and real estate investor.
  • [7:40] How Nav put together the plan and team to launch RealtyShares.
  • [10:36] What the landscape was like when the platform was first started.
  • [16:45] How the initial fundraising effort was so successful (convincing investors).
  • [29:20] What kind of investors can use the platform and what’s the minimum investment?
  • [34:40] Are “family office” investors looking for different things than typical investors?
  • [37:14] The RealtyShares diversified fund and how it works.
  • [41:51] Who is an ideal individual investor for RealtyShares?
  • [44:50] How you can connect with Nav.

Resources & People Mentioned

Jonathan’s Websites


Oct 18, 2016

When you think about real estate development you typically think of the big apartment complex being built in the trendy part of town or the company that’s putting in a new neighborhood down the street. It seems overwhelming to think of taking on a project of that magnitude, but like anything else in life, you can learn how to do it if you approach it the right way. Today’s guest is Steve Olsher, an online personality, author, and entrepreneur who has spent a good deal of time as a real estate investor - and he did so by organizing development projects like the ones I mentioned earlier. How did he do it? Steve tells the story on this episode of Capital Gains.

Making money through real estate development 3 different ways.

As Steve Olsher got started in real estate development he spent time watching what people did who had been doing it for a long time. Through observation and lots of questions, Steve discovered that there are ways to make money at almost every stage of a development project - from the initial closing all the way to management or sale of the project. When I heard him say that it got my attention so I asked Steve how it’s possible. If you want to hear his answer you’ll have to listen to this episode. And I promise you won’t be disappointed.

Steve sees real estate investment opportunities every day as he drives down the street.

Steve Olsher lives in southern California, one of the most expensive real estate markets in the United States. Yet, every day as he drives down the street he sees development opportunities that he is confident could make money. How could that be true? Steve’s background in real estate development is what enables him to see how the changes in neighborhoods and communities, coupled with the existing properties can be leveraged into multi-family unit properties that could even include retail space. That kind of development not only meets the needs of the people moving into a popular area like southern California but it also spurs economic growth. You can hear more about Steve’s insights into real estate investing through development, on this episode.

Here’s how you can get started in real estate development.

After hearing Steve Olsher’s story on this episode I was very curious how he would advise those interested in the possibilities offered through real estate development to get started. So I asked him. His answer was very practical. He says if he was starting all over he’d first do the work it took to meet people who are already overseeing developments in his area. He'd get to know them and find opportunities to come alongside to watch and learn. The benefit of seeing the development process in action when you have no cash involved is unparalleled and powerful. Learn how to make those connections that will help you take the first steps into real estate development by listening to this episode.

Steve Olsher’s new idea for monetizing small followings on social media.

While Steve Olsher has had a lot of experience investing in real estate developments, that’s not all he’s done. Most people know him from his books or his podcast. It’s in that realm that Steve has been thinking most recently. He’s starting to believe that a handful of people with smaller followings on social media could leverage their small following in a cooperative effort with others who also have small followings. Their combined efforts could produce a monetary benefit as a result. He’s not giving away a lot of details at this point but Steve expects that he’ll have something to show the public by the end of 2016. If you’d like to hear more of the ideas Steve’s mulling over, you can hear all about it on this episode.

Outline of This Episode

  • [1:08] My introduction Steve Olsher.
  • [1:34] Who Steve is and what he does (from his own lips).
  • [3:35] How Steve followed each step that was put in front of him over time.
  • [7:17] The path from teen club owner to liquor sales online.
  • [13:40] How Steve made the most of his ownership of after the bubble broke.
  • [16:59] Steve’s steps into writing and radio as a means to add value.
  • [22:15] Where Steve’s entrepreneurial spirit comes from (his opinion).
  • [26:20] The importance of learning the difference between what you want and what you need.
  • [31:20] How Steve got started in real estate investing.
  • [37:20] How developers can make money on deals in 3 different ways.
  • [42:27] The things Steve sees daily that are investment opportunities.
  • [44:40] What Steve suggests for those wanting to get into real estate development.
  • [47:10] Ideas for monetizing a small social media following.
  • [50:24] Steve’s secret ambition (that will no longer be secret after he shares it).
  • [52:30] The best place to reach out to Steve if you feel your story would fit his podcast.

Resources & People Mentioned


Jonathan’s Websites


Oct 11, 2016

Multi-family real estate was not the first real estate investing experience for John Cohen. He has been investing in real estate since 2010 and started out purchasing tax deeds and tax liens, doing $3,247,000 in real estate transactions in 2013. He switched his focus to multi-family properties and joined a group that closed $70 million worth of transactions in one year. Prior to his involvement in real estate, John was a licensed (series 7 and 63) stockbroker but decided that real property investments were far less speculative than the stock market. On this episode, you’ll get to hear why John’s company invests in multi-family properties exclusively, how MF properties are safer investments in a turbulent economy, and what he recommends to those who are eager to invest in the multi-family niche of real estate.

Why is multi-family real estate such a great investment?

Many investors who are trying to build consistent monthly cash flow understand the advantages of rental properties. There's nothing better than having tenants pay your mortgage as you make money on their occupancy of the property they’re paying off. But what happens if the property winds up vacant for a period of time? What happens if the renter is delinquent on their rent payments? Headaches, that’s what! Multi-family properties are almost immune to those issues because the overhead and cost of the property is spread out over many streams of income - the individual renters. On this episode John Cohen will tell you why multi-family real estate is so attractive to him and how you can benefit from being a multi-family investor.

How do you find a good multi-family property?

John Cohen has been investing in multi-family properties for some time. That makes him the ideal person to tell us how to find and invest in multi-family units. On this episode, he gives away his specific strategies for researching a potential real estate market, the exact tools and websites he uses to do his analysis, and drives home the importance of building a good network of brokers and professionals on the ground in the prospective market where you're going to invest. You won’t hear hands-on, relevant advice like this anywhere else, so be sure you listen if you’re at all interested in investing in multi-family real estate.

Why you need to do your homework on location in the market you’re considering.

If you’re considering a multi-family investment property in a city that is not familiar to you, say in Charleston, SC, what are the steps you should take to make sure you understand the local economy and real estate market? John Cohen says there’s only so much you can do online or over the telephone. You’ll eventually reach the point where you need to take a trip to the prospective city to look things over yourself. When you do, there are people you need to meet, specific questions you need to ask, and certain data you’ll need to accumulate from local offices. If you don’t know how to do those things, you’re in luck. John Cohen is on this episode to walk you through it step by step.

How can you invest in multi-family properties if you’re brand new to real estate investing?

One of the questions I asked John Cohen toward the end of this episode of the Capital Gains podcast is how a person who has little experience, and maybe even a smaller amount of cash to invest, can actually get into some real estate investment deals. John’s company specializes in setting up multi-family investment deals and includes a variety of investor types in those deals, so he was happy to give us the full scoop on how it can be done. If you are at all interested in investing in multi-family real estate, John’s got some valuable information for you.

Outline of This Episode

  • [1:08] My introduction of my friend and business competitor, John Cohen.
  • [2:17] What are emerging markets and “value add” properties?
  • [3:47] John’s road to real estate investing.
  • [7:20] What is a Cap Rate and why does it matter in real estate investing?
  • [11:00] What is meant by a “syndication deal?”
  • [16:32] Why John focused on multi-family properties over everything else.
  • [24:19] The types of markets John invests in and the things that attracts him to them.
  • [26:00] How John researches possible investment areas (specific tools he uses).
  • [29:00] Building relationships with brokers and investors in a new area.
  • [32:15] Putting himself on the chopping block, getting outside his comfort zone.
  • [35:53] The advantages and disadvantages of direct ownership Vs being a passive investor.
  • [38:41] How beginning investors can get into REI deals.
  • [45:07] Cautions about working with property managers (and benefits of good ones).
  • [46:25] What is tax deed and tax lien investing and how does it work?
  • [49:57] The importance of a big “why” in real estate and what John sees as his “why.”

Resources & People Mentioned

Jonathan’s Websites

Oct 4, 2016

The venture capital world is growing by leaps and bounds and companies like Flybridge Capital Partners are fueling the tech and innovation behind many of the things that are transforming the world. In this conversation, I talk with Jeff Bussgang, general partner at Flybridge Capital Partners about a variety of things surrounding the venture capital space, including how he got started, what his company looks for in a startup company, and how they assess the leadership and team to make a wise early stage investment.

What IS an early stage investment company?

Early stage investments are nothing more than the money provided to promising companies that are not yet producing their products or services but have made significant headway toward the development or distribution of it. The money they receive is often referred to as “seed money” - the money used to enable the development, marketing, and progress of the company to move it toward profitability and sustainability. On this episode, Jeff Bussgang shares how his interest in the entrepreneurial world led him to become general partner of an early stage venture capital firm, and why startup funding is so exciting.

What is a venture capital investment firm looking for in a startup?

When I asked Jeff Bussgang what the team at Flybridge Capital Partners is looking for in an early stage company he gave me a number of criteria they look at to show them there is promise in the company: Innovative potential, leadership and team, the Pied Piper effect, and more. If those sound a bit vague, don’t worry. As you listen to this episode you’ll get a very clear understanding of what each of those things is and why Jeff and his team consider them vital to discerning a good investment from a bad one. It’s all on this episode of the Capital Gains podcast.

The Pied Piper effect is something startup founders need - at least in this case.

If the team at Flybridge Capital Partners is going to get behind a startup financially they want to see that the primary leader of the startup company possesses what they call a “pied piper” quality. That means he/she is a person who is a natural leader and attracts the interest of people to the projects they are working on. Jeff Bussgang points to the fact that we all know people whose ventures and projects are naturally of interest to us - and it’s because of who the person is and how they are wired that we are attracted. You can almost smell the excitement and potential because they are a person who tends to make things happen. Find out more about this elusive but tangible leadership quality, on this episode.

If you can’t connect with me through a mutual connection, I’m not that interested.

Jeff Bussgang understands that networking and connections are a huge advantage when it comes to making a company or cause successful. So much so that he’s generally unwilling to have serious conversations about funding a startup if their team did not approach him through some kind of mutual connection. He’s convinced that people who know how to make and utilize connections are also the people who will be able to build the relationships that will equip their company for future success. You can hear Jeff make the case himself on this episode.

Outline of This Episode

  • [1:04] Introduction of this week’s guest, Jeff Buskin.
  • [1:54] The types of companies Jeff’s group invests in and what they look for in a winner.
  • [6:50] The “winnowing” process Flybridge uses when evaluating potential companies.
  • [10:50] Signals that a founder or leader is a “Pied Piper” who can build the company.
  • [13:18] What does it mean to be an “early stage” investor?
  • [18:54] Niches Flybridge tends to invest in.
  • [21:58] Sectors on the horizon that Jeff and his team are watching carefully.
  • [24:00] Why Flybridge has a geographic bias toward Boston and New York.
  • [25:23] Why relationships matter so much to Flybridge.
  • [31:23] Jeff’s path to Flybridge.
  • [36:58] The tendency toward entrepreneurism: Is it innate?
  • [39:03] Successes the company has had and what they have learned.

Resources Mentioned


Connect With

Website: On Youtube On Facebook On Twitter On LinkedIn

Sep 27, 2016

If you want to learn how to network with the people you most need to meet, nobody can teach you how to do it more effectively than my guest today, Judy Robinett. I came to know about her through reading her book, “How To Be A Power Connector.” Through the book, she opened my eyes to a systematic way to connect with people that influenced my thinking significantly. I invited Judy on the show to talk about her book, but also to share her experience in the angel investing niche - which is significant. Those are two ways you’ll benefit greatly from this conversation, so I hope you take the time to listen.

As soon as you learn how to add value to people quickly, you get noticed.

Networking used to be nothing more than going to business meetups and exchanging business cards. But even back then, those who knew the “secret” recognized that it wasn’t about being at the meeting to blast out your name and business to others, it was about adding value. Judy Robinett says that those who learn to add value to people quickly, get noticed quickly - and it’s that kind of attention that puts you on their radar in ways that can move your business endeavors forward. Judy unpacks that principle and a whole lot more on this episode, so be sure you listen.

Do you know how to get a warm introduction to someone you need to know?

It’s so much easier to start a conversation with someone you need to meet if someone they already respect or work with introduces you to them. That’s called a “warm introduction” and it’s not always something that’s easy to come by. But Judy believes that anyone can learn how to get those kinds of introductions - to almost anyone on the planet - if they know how to go about it. On this episode, she shares her two “golden questions” and tells you how to use them to make connections with the people who matter. You won’t want to miss this simple but powerful tip. It’s so obvious it’s embarrassing that I hadn’t thought of it before.

Anything you need is attached to people. You need to connect with them.

Judy Robinett points out that since the average person knows 600 people, it’s likely that almost everyone you meet is connected to someone that would be beneficial to you or your business. Said another way, the resources and introductions you need the most are only a few relationships away. But you have to know how to go about discovering those relationships and how to go about getting the warm introduction you need. Judy is a pro at doing that and in this conversation he tells me some of the ways she has gone about connecting with high profile people in all industries, government, and more.

Don’t ask for help right away, ask how YOU can be of help.

One of the foundational principles of power connecting is that you play the long game. Patience is indeed a virtue. Find out what other people do. What are their dreams? Then think of the ways - through your resources and connections - that you can advance what THEY are doing. In this way, you become an asset to them that they won’t easily forget. When the time comes that you need to ask for a favor or introduction, they’ll respond in light of the value you’ve already provided to them. In other words, they’ll trust your motives because you’ve already been generous to them - and they’ll be eager to help. Judy Robinett is my guest today and she shares a lot more tips like this one, on this episode.



Outline of This Episode

  • [0:24] My introduction of Judy Robinette and this episode.
  • [1:38] Judy’s path to becoming an entrepreneur and influencer.
  • [6:00] How Judy learned how to develop her power connecting skills.
  • [8:22] The 5-50-100 rule for establishing and maintaining connections.
  • [10:30] Judy’s two golden questions for strategic networking.
  • [12:52] How should a startup founder go about finding capital funding?
  • [16:30] What is a warm introduction and how do you receive one?
  • [19:59] What is a “good deal” to an angel investor? What are they looking for?
  • [22:37] How an advisory board fits into a startup/investment scenario.
  • [27:20] What an investor could do to become familiar with angel investing.
  • [31:31] What it means to do “due diligence” when checking out a startup company.
  • [34:47] What are angel investing teams looking for in investing partners?
  • [41:26] How to respond to a deal that comes to you privately.
  • [44:27] Judy’s biggest mistakes in angel investing and what she learned from them.
  • [47:12] Big projects Judy has in the works.
  • [49:38] How you can connect with Judy.

Resources & People Mentioned

Sep 20, 2016

Seed funding in a specific niche.

My guest today is Razi Karim, CEO of Bayside Venture Partners. Razi and his team focus specifically on investing in early stage companies that they see as potential successes in T.I.M.E. - Technology, Intelligence, Media, and Entertainment. Razi sees their company as a “Micro VC” company, an early stage accelerator. On this episode, you’re going to hear Razi describe the many ways his company comes alongside early stage companies to both advise and fund them toward the path to success.

Invest early at low cost.

That’s the strategy that Razi and his team follow as they consider startups that are in need of early stage investing. They want to make wise decisions about whether to invest in the company of course, but once they do make the decision to fund a company they want to do so in a way that allows them to ride the wave of success as the company raises funds, builds out its infrastructure, onboards users or clients, and begins to make a splash. You can hear how Razi guides his company through everything from initial conversations to negotiations, to full on seed funding in an early stage company, on this episode of the Capital Gains podcast.

Red flags in startup companies that will prevent seed funding.

Naturally, every seed funding source is going to have its own criteria for what would remove an early stage company from funding consideration. Razi ????? and his team have discovered that there are a handful of things that indicate that the company or its team are not quite ready for the kind of support that Bayside Venture Partners (Razi’s company) are able to give. If you’re an early stage company that will eventually seek funding, you’d do well to know Razi’s list so you can do everything possible to be an attractive opportunity for your investors when that time comes. You can hear his suggestions on this episode.

How should you approach a possible investor to seek seed funding?

The world of venture capital and seed funding is new to most startup founders so it’s good to have an experienced voice that can speak to the issues involved. Today’s guest, Razi Karim gives a handful of suggestions to teams that are seeking or will soon be seeking investments in their early stage company. His suggestions range all the way from team dynamics and business model to already existing customers or users, as well as the attitudes he looks for in the leaders of new companies that tell him they will be a great partner to work with.

If you have funds to invest in early stage companies, what should you do?

Many people who are actively investing are tired of the stock market, don’t believe in the return on bonds, and are open to other options. If that is you, it’s entirely possible that you could invest your funds in early stage companies. Razi Karim suggests that you find a group that invests in companies like you are interested in that has a track record of experience and good returns. The company's team should also have an eye toward identifying and evaluating the talent and opportunities that early stage companies bring to the table. You can learn more about how you can go about seed investing, on this episode of The Capital Gains Podcast.

Outline of This Episode

  • [1:07] My introduction of Razi Karim and his company Bayside Venture Partners.
  • [2:04] What is a Micro VC?
  • [2:33] Understanding the terms used in venture capital investing.
  • [5:14] The types of companies Razi looks at to invest in.
  • [7:58] The growth and status of Razi’s investment company: Invest early at low cost.
  • [10:59] Razi’s process of looking for and investing in an appropriate company.
  • [14:46] Signals Razi looks for in potential investment opportunities.
  • [18:10] The percentage of deals Razi takes on compared to those he considers - and the things that makes a company stand out as a winner.
  • [19:33] The product VS the team. Which is more important?
  • [23:41] The advisory services Razi’s company provides and where it fits as a service.
  • [27:50] How Razi got into angel investing in the first place.
  • [31:35] What is an accelerator and how does it work?
  • [34:26] How Razi advises startup founders to approach possible investors.
  • [36:44] What should a person do if they have money to invest and are curious about venture capital investing?
  • [40:50] Lessons learned on the journey.
  • [43:20] The vision and future of Razi’s company - as he sees it.

Resources & People Mentioned


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