The Five Pathways to Real Estate Investing Success


This past Friday afternoon, with eight house flip deals all going at once, I just didn’t have time to volunteer at The Bourne Scallop*** Festival.

With everything going on and it being a Friday, it was the last thing in the world I really wanted to do.

But there it was, across the street from my offices in Bourne Massachusetts was one of the largest events on Cape Cod each year – sponsored and backed by my local Cape Cod Canal Regional Chamber of Commerce.

***For those of you who are not from Massachusetts “scallop” is pronounced “SKAAAH – LOPP” not “SKAY – lupp” by the way 🙂

The Chamber had asked me to volunteer and I accepted – and although I had no time to do it – I went with my partner Ralph anyway. We took out the trash, cut lemons, cleaned up the food service area and generally did anything we were ordered to do.

I can’t say either one of us really enjoyed doing it…but both of us had made a promise and we were going to stick to it.

Could I have called and told them I couldn’t make it? Could I have just not shown up and blown off the whole thing?

Don’t get me wrong, all those thoughts DID occur to me…and I was tempted to back out and just do my own stuff. And as I was thinking this, I also realized that I had a prescheduled “date night” with the lovely and talented Christina LaCava that night that I couldn’t possibly cancel. So it made the Scallop Festival thing even more of a pain because I couldn’t catch up on my work after my shift was over…

So I sucked it up and did it.

And although my real estate investing business was put on hold for most of Friday, I was none worse for the wear. And even though everything was put on hold for the better part of entire day, I was still was able to join Christine for a great meal at one of our favorite local restaurant that night.

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House Flipping Success One Step at a Time

After my crazy Friday and time with my wife, Saturday’s alarm clock came way too early.

I had an appointment to walk raw land for a development opportunity with a friend of mine. We had to meet at 7 AM – ouch!

There’s a chunk of land in Wareham and we had to figure out a way to get in three houses into the property and do the build out for a road and develop the land at the same time.

I’ve never bought undeveloped land before – and doing it is a complex process because you need to know a lot of things that are pretty foreign to me such as lot numbers and sizes, infrastructure, abutters, offer amounts – all things I’m vaguely familiar with, but nothing I’m an expert at.

My friend who was showing it to me was someone I’ve known for more than 30 years – so learning from him would require me to either hire him as a consultant or have him become a partner in the deal. Since I know next to nothing about land development, I’d have to either cut them in or do some coaching with them to learn how to develop the land.

After the walk on the land, I then rushed off to a business planning meeting I had set up with my House Flipping School business partner. For five hours, we hashed out all of our goals for the next 15 months – including live events, online activity, mission statement and our local real estate developmental involvement plan.

All the while, the phone is buzzing with calls from contractors, private money guys and of course, my lovely wife.

Just another day in the life of a real estate investor…

What Will You Do To Be Successful?

Is “success” a step by step formula with a smooth unbroken path to riches?

Some people think so. But I’ve found it’s not just one thing at all. Rather, it’s a mosaic of thousands of decision you make all adding up in a somewhat organized fashion to achieve your desired end. And the last 24 hours, although it may not have seemed like I was working my success plan at all times, in actuality, I was.

What do you think the path to “success” is?

Needless to say, it was a busy couple of days – and I am in no way complaining. But the one thing that’s a constant in all of this is that everything I was doing (even the date out with my wife) had a specific objective in mind – and many that are more far-reaching than just “how much more money am I going to make on my next flip?”

Five Pathways to Success

If I were to break down the steps to success for people – whether it’s in life or in real estate investing, many of them would include the things I did in the last 24 hours – not all of them, but quite a few.

The difference was that I was doing them instead of just saying them. Here they are more specifically:

1. Give Back

Make sure you always make time to give back to the people and the communities in which you work. Whether it’s volunteering at The Bourne Scallop Festival, at a local soup kitchen or joining Habitat for Humanity; always give back. You may not THINK doing these things will help your business, but they actually will – although you may have no idea how it will help you when you’re doing it – the act of actually doing it sometimes is the reward in itself.

Truth be told, I owe a debt of gratitude to the local Chamber of Commerce here in Bourne. No doubt, I have gotten my fair share out of being a member for the past nine years. And although I had a million other things to do on Friday, I put all those tasks aside to show some appreciation to the group who helped me launch my real estate investing business nearly five years ago.

2. Try New Things Outside of Your Comfort Zone

Land development is a tricky business and its one I know next to nothing about. But I’ve always wanted to do it and learn about it. As I mentioned on the modular home I did last month, I got a taste of development, but now I’m learning to do it.

Its uncomfortable being so green – but how else are you going to learn? Whenever you get out of your comfort zone, become a “newbie” all over again, you’re helping yourself expand and grow. And when you do these things, you can’t be concerned with looking foolish, just go for it.

3. Set Goals

Without goal setting, you’re really just dreaming. Take time away from your business, take a step back and set some goals for what you want to achieve. In our strategy session on Saturday, we did just that – laying out or business goals on a big whiteboard and then backing it up with a word document that will be the guiding force for all the action we take in the next 14 months. After crafting it, I felt like every goal we laid out was possible – because we had stated our goals emphatically on a document and had a specific plan to make sure we achieve it.

4. Create Your Own Mission

As I said, our business is gaining a ton of momentum – so much so that we really have to make sure we set the proper course and fulfill our obligations as teachers and stewards of the “house flipping” moniker.

Although one of the goals of our real estate educational platform is to make a profit – the REAL goal is actually far more than that. Although it may be lessening somewhat, “house flipping” still has a reputational issue – and righting that misperception is a dual goal  of our real estate educational platform.

We feel our mission is to be responsible real estate investors – but in so doing, do the following:

  • Create economic development
  • Restore neighborhoods
  • Put people to work
  • Create community quality of life improvements
  • Create affordable housing
  • Improve the local economy

Our business planning session was on how we are going to achieve these objectives with local meetings to not only educate and create community – but educate new real estate investors do the very same thing.

And on a crystal clear Fall Saturday afternoon, there we were inside my office – hashing out the objectives and mission of how we can help new real estate investors to not only be successful in making money investing in real estate – but doing it so they help achieve the greater objectives in our mission.

5. Take Care of the Home Front

Although this is not a step to success that any real estate investing course will EVER give you, for me, it’s one of the most important. If you are spending all this time on your business, growing it and working towards even greater success, don’t forget to take everyone who is close to you along for the ride.

If you’re all about work, work, work and forget to have a date night with your wife or take your family out for pizza or help your daughter move into her new apartment because “you’re too busy on your business” – then what the use? Because when you achieve your success, you’ll all of a sudden realize there is nobody else on your team – and the taste of success is all the sweeter when you can share it those that you love.

Yes, there will be times where you simply can’t make your daughter dance recital or your son’s soccer game or you have some emergency come up so you have to cancel dinner with your wife…but make those the exception instead of the rule.

Make sure you always take care of the home front first and when you do that, believe it or not, your success in your business life will come faster…not to mention it will be a whole lot sweeter.

All lessons I learned because I had to volunteer at a Scallop Festival….

How about you? What do you think is most important? If you made it this far, leave a comment below and tell me what you think!

Photo: Stuck in Customs

About Author

Mike LaCava

Michael LaCava is a full time real estate investor, house flipping coach and the President of Hold Em Realty located in Wareham, MA. He runs the website House Flipping School to teach new real estate investors how to flip houses and is the author of "How to Flip a House in 5 Simple Steps".


  1. Larry Weingarten on

    Mike: I don’t comment much, but you’ve done an exceptional job of describing the art of balancing different and sometimes conflicting goals. You have made clear how important it is to be a contributing part of your community. Nice post! Thankyou.

  2. Mike-

    What a great post. Entrepreneurs have the tendency to think that our businesses will come to a halt if we take some time off for any activity. And it’s hard to justify some of the things we do (time wise) like you did on Friday. But the truth of the matter is that all of these things tend to have a positive effect on our businesses; we just might know how that will come about at that exact moment we do them. Finding balance in our lives is tricky business, but we have to continually strive to find it.

    Your planning meeting sounds awesome. The fact that you actually followed through on your plan to map that time period out is in itself a huge step forward. So many people (myself included) get “caught up” in the day to day activities. Planning time and setting aside time to think are critical to your success. In order for it to get done, it needs to be scheduled.

    Good luck on your new investing strategies.


    • Thanks Sharon – Tough to shut the thinking down when you are growing your business although necessary. A few days in Vermont last weekend with limited internet and cell phone service was nice. Chilling watching the Patriots today and some golf but thinking about my day tomorrow. LOL.
      Good thing I love what I do!

  3. Stephanie Dupuis on

    Really enjoyed your post, Mike. I had a discussion with a friend this week about the importance of following through on promises to family and other commitments when REI is “happening”. My last j.o.b. fortunately taught me this and it is a constant struggle. Makes for some long and exhausting days, although worthwhile and memorable. Like you, I often feel like backing out but never do. An internal struggle – I already know the answer but waste time dialoging in my head (time to stop that, now that I’m writing it!).

    I respect your new projects. One of my favorite mentors was one I had when doing my teaching internship. He’d frequently say, “When you’re green you grow, when you’re ripe you rot.” Yup! 20 years later I hear his voice in my head each time I need to learn something new, stretch my skill set, or make a mistake.

    Thank you for sharing your story – helps us all with the reality of REI and the importance of personal growth and family.

  4. First off, I am hungry now. Secondly, very good article on the mindset a person has to have to make goals happen. You cant achieve goals by sitting on the porch in a rocking chair talking about it. Go get your hands dirty!

  5. One of the best posts I have read on any blog or forum. Sometimes its easy to forget why we do this thing called entrepreneurship. Certainly independence and the chance to build your own wealth rather than someone else’s, but for what? Whats the purpose? Freedom? Freedom from or to what?
    For those that are fortunate to call their significant other “Best Friend” and love being with their kids and friends. This can be exactly the punch in the face we occasionally need when we get too ambitious or focused.
    I find the most joy from focusing outside myself(To include RealEstate along service), although it can be counterintuitive in a culture(both business and pop) that screams “get yours”.

    Thanks BiggerPockets and Michael,
    Great Post!

  6. Michael-

    I especially like #5. Whether it’s a gift card, or taking a key partner to Los Cabos, you’ll usually get more than you give! It may not be immediately quantifiable, but people work with those they like. They will go the extra mile for others who show appreciation for them. I remember one woman at a title company who I complimented on a verse in her email signature. She said I was the first person to ever notice!

    Great article.

  7. Another good thought provoking article Mike.

    I really like the last one about taking care of the home front.
    Like you said if you always put people off because you are too busy with work – What is the point is right!

    Though at the same time I think a lot of times entrepreneurs are extra hard on themselves since we do have flexibility. Sometimes you do have to do something for work and miss a personal event and it is okay. If you had a J.O.B. nobody thinks anything of it since someone else is telling you that you can’t go to these things (and usually you will miss out on a lot more!).

  8. Charlie Williams on

    Great article Michael. Especially #5. It is so easy to get wrapped up building my new business that I forget to do the little things with the family. Both my kids are teenagers and in a few short years they will be out on their own. I definitely will make more of an effort to take that break from work to spend quality time with them and the wife. And yes it will be so sweet when I reach my goals while taking care of the Home Front. Thanks for reminding me.

  9. Mike Fitzgibbons on

    Hi Michael,
    Cape Cod represent! What a great article. I’m just getting started looking for flips and I am certainly a “newbie” as I’ve only had my license for 6 months. I work as a part of a team and I do the scouting, comps, and some of the later marketing. It’s very competitive on the Cape so I’m lucky that my investor saw something in me and decided to give me a chance. Everyone starts somewhere. We made lots of offers and we closed one deal so far. We are always looking for more. I’ve basically been cold calling and using traditional searches via MLS but I am really looking for better ways of finding property before it goes on MLS. I have some connection with Fannie Mae so I’m always aware of some pre-listings but I know I need to network further. I’m really interested in cheap/free prospecting ideas too. Does the Cape have any meetups or do you find yourself travelling off Cape for meetings?

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