James | Gladstone Profile Banner
James | Gladstone Profile
James | Gladstone

@glad_cap

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Quit BCG to mow lawns. SMB | RE

Boston, MA
Joined February 2020
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@glad_cap
James | Gladstone
2 years
Quick background for everyone I haven’t met yet: - Boston area small business owner by way of buying a residential landscaping co in March ‘21 (note: try to not buy a company 2 mo before having your first baby) - Previous work chapters included time at PwC and BCG, where…
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@glad_cap
James | Gladstone
3 years
Pre SMB office --> new office... trying hard to remember (convince myself) that this is an upgrade.
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@glad_cap
James | Gladstone
4 years
Putting in an LOI to buy a small company that manufactures, sells and tests building safety equipment. ~500k SDI on 1.2 gross, asking 1.7. First on-site went well. What are the overlooked questions I should drill down on @sweatystartup @laughridge @StrongpointRich
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@glad_cap
James | Gladstone
2 years
My playbook for buying a small business while still working a day job:
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@glad_cap
James | Gladstone
3 years
There's a myth that us corporate folks can buy a small home-service business and simply apply our "business skills" to boost revenue and trim expenses…
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@glad_cap
James | Gladstone
2 years
Current tech stack for $1.2m landscaping company (mostly maintenance): • Banking - Bluevine (internet), Citizens (local) • Credit Cards- Divvy, Chase, Wex (fuel cards) • Accounting - QBO
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@glad_cap
James | Gladstone
5 months
@NeelBParekh even better than points are mistake fares... $200 round trip boston to dubai, went with 3 friends for a few nights to play Majilis. $250 round trip in first class to Greece for a friend's wedding There are usually 4-6 absolutely killer mistake fare deals every year if you're
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@glad_cap
James | Gladstone
5 months
@jasontheseoguy @NeelBParekh Twitter is great - there are a ton of accounts with price / mistake fare alerts. @TheFlightDeal @TJBdeals @DansDeals etc.. My SIL also runs so I get the inside scoop on some things from her. ... but almost 100% of everything in the travel deal world
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@glad_cap
James | Gladstone
2 years
One piece of advice to anyone looking to buy a small business: Don’t let someone else’s limiting beliefs dictate your path. I broke a lot of “rules” (bought “too small,” kept my w2 job while searching AND operating for a full year). Make your own rules.
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@glad_cap
James | Gladstone
2 years
Officially hooked on @myfirstmilpod . @ShaanVP and @thesamparr seem to genuinely enjoy hanging out together and letting the listener into the conversation. ++ great interviewers with unique / fun questions. Closest business podcast I’ve found to something like pardon my take.
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@glad_cap
James | Gladstone
10 months
Worst question I was asked at the hbs eta conference: “Do you miss working with quality people?” If you’re talking to a current owner/operator, this indicates a severe lack of empathy and appreciation for people working in the SMB world. The people that keep roads plowed,
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@glad_cap
James | Gladstone
4 years
Made it through underwriting on the landscaping biz. Things are getting real!
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@glad_cap
James | Gladstone
1 year
Just hired a guy to come fill our trucks / gas cans up overnight. He has degrees in: * Finance / Accounting (Texas Tech) * MBA (Cornell) * MS in computer science (U Penn) And he is currently filling the gas tank of my 2003 Accord as a demo. What a world we live in
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@glad_cap
James | Gladstone
2 years
I am almost always trying to open new lines of credit (especially when I don't need more cash). The #1 rule of an owner is to not run out of money. The best time to look for money is when you don't need it. Here's a few ways to line up cash before you need it:
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@glad_cap
James | Gladstone
4 years
@ConorNeu @roblabonne @moseskagan @sweatystartup On my first #multifamily purchase, seller gave me hand written financial statements
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@glad_cap
James | Gladstone
2 years
Weeks after closing on my business, our #3 guy passed away from a heart attack. What do you say to the team? How much $ do you give to the family go-fund-me to bring body back to Brazil? Knew owning a biz meant making hard decisions, but had no idea how to handle this.
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@glad_cap
James | Gladstone
2 years
Started going down way too many rabbit holes trying to get a base of SOPs set up. The prospect of "documenting my business" is both exhilarating and debilitating. My antidote is to just make shitty progress. Open a google doc and start writing.
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@glad_cap
James | Gladstone
4 years
@JesseTinsley @Keith_Wasserman I made my own weight plates out of concrete and pvc. Fun quarantine project!
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@glad_cap
James | Gladstone
3 years
Big day... first official payment received as a new SMB owner / operator. Small check for taking down holiday lights, which I did myself, on a 10 ft pruning ladder, at 6pm last Friday, 100% I was going to fall and break my legs and end my SMB career before it started.
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@glad_cap
James | Gladstone
2 years
Kind of glad I procrastinated on creating more of our documentation now that the internet can basically do it for me.
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@glad_cap
James | Gladstone
2 years
There are only two books you should read if you want to buy a small biz: 1. HBR Guide to Buying a Small Business 2. Built to Sell
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@glad_cap
James | Gladstone
1 year
@AlexHormozi I agreed with this… until kids. Kids aren’t in school on weekends and it’s the time you get with them doing fun activities, going away on day / weekend trips and doing all the things that you work for. It’s when friends / family are available to hang out, the best concerts /
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@glad_cap
James | Gladstone
5 months
@MrJonesSTRs *** PEST CONTROL, no one budgets for this but it should be 100% included for every airbnb... no one wants the review: "Woke up next to a rat. Would not return"
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@glad_cap
James | Gladstone
9 months
@thesamparr There's a similar doc about WW1 - equally as fascinating (They Shall Not Grow Old, also on netflix). WW1 doesn't get as many movies / docs as ww2, but those trenches were no joke
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@glad_cap
James | Gladstone
3 years
Assume that maybe, just maybe, you're not as smart or hard working as you tell yourself and others. Give yourself more time, capital, and grace than you think you'll need. Be ready for the punch, and come back swinging.
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@glad_cap
James | Gladstone
1 year
Closed on 2nd acquisition today, small tuck in which will add some good density to our routes. Feeling a little buyer remorse and definitely overpaid, but excited to get reps in integrating new companies and getting the word out to other local owners that I’m buying. Any tips
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@glad_cap
James | Gladstone
3 years
Speed wins. Gave this guy a quote a few hours after our on site assessment. He wanted to get quotes from lower cost providers. Two weeks later and he hasn’t heard back from anyone else.
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@glad_cap
James | Gladstone
3 years
Alright guys - I’m back. It’s been a while since I tweeted, but I now have both a business and a baby. On all fronts I have absolutely no idea what I’m doing, but having tons of fun doing it. More to come on the business acquisition and first few months operating
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@glad_cap
James | Gladstone
2 years
@shawngorham Do you actually register the car etc before re-selling? Seems like sales tax and the time lag would eat into profits.
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@glad_cap
James | Gladstone
4 years
Sundays I like to organize my 10000s of to-do items / thoughts into one coherent list and start scheduling + organizing tasks. This is the 1/2 way mark. I *should* close on the landscaping co. Thursday - and have already sent out my first estimate and hired 4 new techs 🙃
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@glad_cap
James | Gladstone
3 years
The owner you bought from? She has 20 years of learned intuition at her disposal. She knows how to fix every piece of equipment - and knows when it's worth replacing vs fixing. She knows where to cut corners, and where to double down on quality.
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@glad_cap
James | Gladstone
3 years
@sweatystartup Clearly a Pidgey. I’d recommend an electric Pokémon like Pikachu. One shot kill no problem.
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James | Gladstone
2 years
One mistake I made after buying a small business was waiting too long to get our books in order and comprehensible. It was months before I could answer simple questions like “how did we do last month” or “do we have enough cash until the next batch of invoices go out”
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@glad_cap
James | Gladstone
4 years
#SMBTwit - are you guys doing hand written notes? How about specific, solution based marketing? Got this in the mail and thought it was really effective. @NickHaschka @chenholdco @StrongpointRich
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@glad_cap
James | Gladstone
4 years
@sweatystartup “We should do some more shots”
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@glad_cap
James | Gladstone
3 years
Probably not - and definitely not without a lot of sacrifice, mistakes, and a whole new perspective on anxiety. This game is harder than you think
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@glad_cap
James | Gladstone
1 year
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@glad_cap
James | Gladstone
1 year
@LeadershipAcad1 Took ours a step further
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@glad_cap
James | Gladstone
6 months
@Camp4 I did the same thing a few years ago!
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@glad_cap
James | Gladstone
2 years
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@glad_cap
James | Gladstone
3 years
@Austen All it takes is one big win
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@glad_cap
James | Gladstone
2 years
The main point is you absolutely do not need to quit your job to start looking for a business to buy. Most of this can be done on nights, weekends, and maybe a few lunch calls. It helps to buy local and small / simple, but I don't see why it can't work further away.
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@glad_cap
James | Gladstone
2 years
Value—> when one tweet turned me onto a 100k tax credit (we qualified as a recovery startup business). Immense thank you @baldridgecpa !! Owe you a beer or 50 some day.
@baldridgecpa
Mitchell Baldridge
2 years
Over the last two years US business owners have received over a TRILLION dollars of economic relief. Most of these programs have ended, but affected employers still have access to one that can pay thousands to millions. The Employee Retention Tax Credit (ERTC) Thread 👇🏼
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@glad_cap
James | Gladstone
4 years
Our first Airbnb is all buttoned up and ready for action! Very proud of my (pregnant) wife for running the show on this one and getting it it from closing to launch in two weeks. What a boss!
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@glad_cap
James | Gladstone
2 years
Had to let a few guys go yesterday. All great people who I genuinely liked to be around, but we couldn't get over a few recurring issues. First time I've felt this mix of sadness and lightness at the same time.
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@glad_cap
James | Gladstone
2 years
@EstateRanger Limits to LLCs for asset protection and anonymity (especially if single member LLC like most people will do). For a single family rental property, you’re fine keeping in personal name, bump up insurance and buy and umbrella policy. Or, put in a trust… maybe better than LLC.
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@glad_cap
James | Gladstone
7 months
@moseskagan What logins make you the most nervous? I use lastpass for everything so they can access what they need but never actually know the passwords. Most systems have decent access controls at this point for read/write functionality as well.
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@glad_cap
James | Gladstone
4 years
What are some good gift ideas for LPs? Something thoughtful but won’t break the bank. @StrongpointRich @laughridge @NickHaschka @sweatystartup @AlbaumMichael @roblabonne
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@glad_cap
James | Gladstone
4 years
Sold! This Boston area duplex was one of my first bigger rehab. After holding as a rental for two years, it was time to sell and let the new owners enjoy! Here are a few things I learned on this one:
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@glad_cap
James | Gladstone
10 months
@Slackwatercap Just had the exact opposite situation and it made my day (got this text from our office manager). The SMB roller coaster is real.
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@glad_cap
James | Gladstone
4 years
@urbnist @TheRealEstateG6 The best time to plant a tree is 20 years ago. The second best time is today.
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@glad_cap
James | Gladstone
2 years
@Jacxonic I'm doing this today
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@glad_cap
James | Gladstone
1 year
Simple 'north star' KPI we're tracking reviewing this year (residential landscaping): Realized direct labor rate ... meaning: billed labor revenue / total paid work hours Simple to do this manually every week (always something to adjust). Target blended billing rate is $95
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@glad_cap
James | Gladstone
3 years
Let’s party @aebridgeman
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@glad_cap
James | Gladstone
3 years
Amazing description of exactly what I’m going through. Will add to the list that there is no one telling you what to do or telling you if you’re doing a good job. Takes a lot of “intestinal fortitude” to make tough decisions (like @MikeBotkin_ firing all of his customers)
@J_M_Vogt
Justin Mazeka Vogt
3 years
So you want to start a Holding Company... See Chenmark's description of "the early days of compounding" before getting too starry eyed
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James | Gladstone
4 years
@jackbutcher @TihoBrkan Just started digging in on a $1m landscaping business that has no website, no email, no online reviews, and only takes checks...
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@glad_cap
James | Gladstone
3 years
Now, we don't take on any projects for non-maintenance customers. We have residential clients who spend $70k/yr with us and never question a quote or invoice. Serving our existing clients better will pay far more return on headache than taking on projects with unknown clients.
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@glad_cap
James | Gladstone
3 years
This company still uses fax machines! There's no CRM, no email marketing, not even a website! If BobVanceRegrigeration @aol .com can take home $250k on $1m in revenue, surely you can do better, right?
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@glad_cap
James | Gladstone
3 years
Baby’s first rental property!
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@glad_cap
James | Gladstone
3 years
Me last year: let's chill out and stop committing to so much. Me this year: I can totally buy a business, work a full time job, have my first kid, go to business school part time, continue building my real estate portfolio, finish our basement and solve world hunger.
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James | Gladstone
3 years
None of this knowledge lives outside of the owner's brain, and you'll come in completely blind to the fact that these problems even exist, let alone how to solve them.
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James | Gladstone
2 years
@MikeBotkin_ Have you looked into booster fuel (they come and fill everything overnight, no fuel tanks on site required)
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James | Gladstone
4 years
@Nick_Keesee From my first 6 unit:
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@glad_cap
James | Gladstone
4 years
@laughridge I think you're underestimating how much people want Chick Fil A on Sundays. Wayyyy more than a 16% bump.
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James | Gladstone
3 years
This was a fun project - irregular bluestone steppers with Irish moss in the joints for a more organic feel. Like finishing a big puzzle with no box to look at.
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@glad_cap
James | Gladstone
4 years
@TheRealEstateG6 The single best real estate networking spots that no one ever uses are planning / zoning meetings. You have teams of people ACTUALLY BUILDING THINGS all huddled together.
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@glad_cap
James | Gladstone
3 years
If you think you can just waltz into a 20 year old small business and dramatically improve things with your corporate know-how... you're likely in for a rude awakening. Don't sell that BS to yourself, let alone your life or business partners.
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@glad_cap
James | Gladstone
4 years
@shaneconneely7 @EstateRanger For small time landlords the best option is @CozyCo . For professional PMs or owners managing a big portfolio, it’s @AppFolio
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@glad_cap
James | Gladstone
4 years
This morning I'm reflecting on how fortunate I am. A bank just lent me over $1m at 3.24%. $100k cash out refi and my monthly payment went DOWN. 18 year old James would have a tough time making sense of this. #retwit #realestateinvestor
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James | Gladstone
4 years
@laughridge and @aebridgeman took from "kind of interested" in the SMB world to getting my first company under contract. Can't wait to listen to this!
@aebridgeman
Alex Bridgeman
4 years
My conversation w/ @laughridge on: - Blending RE and SMBs - His wife's store Nell Hill's - What drives key employees - Using SBA loans to acquire co's - Why Brandon moved away from online businesses Enjoy!
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James | Gladstone
4 years
@joepohlen @StrongpointRich @laughridge @NickHaschka @sweatystartup @AlbaumMichael @roblabonne Got a really nice handwritten note from one of my agents and it definitely made an impact on how I feel about his team.
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James | Gladstone
2 years
@joshuamschultz • Health Care reimbursements: TakeCommand health • Google suite for email, docs, sheets etc. • Phone: Openphone - love the shared texting • Communication: slack (admin only), good old texting
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@glad_cap
James | Gladstone
9 months
One of my local industry acquaintances is pushing hard to try to poach my #2 / ops manager (who is awesome). Called him 3x last week. He (ops mgr) told me about it and says he has no interest in working for him. Is this shitty or all part of the game? My view: if someone
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@glad_cap
James | Gladstone
10 months
@RobertMSterling I grew up in an affluent town. Try to remember that I often had more fun in beat up civics than new beamers. My favorite house to hang out at was old and cold and creaky, but had an unfinished basement with a ping pong table and a hockey net against the wall. Great back
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James | Gladstone
3 years
Owning short term rental properties is all fun and games until your town bans them overnight. #REtwitter - would you ride it out or sell it off?
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James | Gladstone
3 years
@StudentRentPro We gutted our place 2 years ago and my most recommended things to friends are: 1. Heated floors wherever you can but especially bathrooms 2. Instant hot water tap in kitchen sink 3. Light switch / outlet placement 4. Don’t rip off your roof right before a global pandemic
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James | Gladstone
3 years
So how can you prepare to get burned? 1. Scenario planning: How would you adapt to a 30% increase in labor prices? What would you do if 1/2 your trucks broke down on the same day? What if your GM quit the day after closing? If it hurts to think about, it deserve attention.
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James | Gladstone
10 months
@AutomationMrktg *backhand slapped to Connecticut* Something to the effect of- I work with a ton of quality people now, so I'm not sure what you mean by that. It's a different skill set than PwC / BCG, but most of my former colleagues probably wouldn't have gone out plowing on Christmas
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James | Gladstone
8 months
@ShaanVP @girdley I’m not 100% sure it’s a bit tbh
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James | Gladstone
2 years
@Adrian_Pinto2 Decided that we won’t let labor shortage hold us hostage to employees that don’t meet our standard. Let 4/11 guys go and I can’t tell you how much better last few weeks have been for me AND for the high performers on the team.
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@glad_cap
James | Gladstone
3 years
Sometimes you just need to burn your hand on the stove to believe it's hot. And that's ok. The danger is in not planning for the burn.
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James | Gladstone
4 years
2 guys and 30 mins for a sewer camera. $400 for the pleasure. And now I’m thinking the drain business is kind of interesting. @StrongpointRich you guys do drain clean outs / cameras? Also yes I obviously smash that 55lb kettlebell all day.
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James | Gladstone
2 years
@ClintFiore Having a house cleaner
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James | Gladstone
2 years
1. Read 1-2 books MAX to get a baseline understanding of what you're in for. Don't spin your wheels reading more than that.
@glad_cap
James | Gladstone
2 years
There are only two books you should read if you want to buy a small biz: 1. HBR Guide to Buying a Small Business 2. Built to Sell
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James | Gladstone
6 months
@LeadershipAcad1 Ramp rack 💯
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James | Gladstone
2 years
Leaving Wednesday to spend 3 weeks in Cape Town. Wife already booked shark cage diving and surf lessons and updated our life insurance policy (probs). Excited for a fun adventure. Not excited for 18 hour flight w/ a 2 year old. Who else loves traveling this time of year?
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James | Gladstone
8 months
@moseskagan In our market the issue is that so much goes through variance. Development is so intimidating if you’re not living and breathing it (maybe that’s for the best since it’s so challenging). In Boston almost every new development, even something like a 4 unit condo building, is
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James | Gladstone
4 years
Top 3 offers on duplex I’m selling: 1: 650k w/ inspection, conventional loan 2: 645k ‘information only’ inspection, VA loan 3: 640k no inspection, conventional loan Units were 75% gut rehabbed Who ya got @JumpInRE @Codie_Fisher @AlbaumMichael
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James | Gladstone
2 years
@DevinWanzor Spent $10k w/ wife, traveled for 6 mo through NZ, Southeast Asia and Japan. Spent a lot of time volunteering in random places in exchange for food and housing. Life changing experience.
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James | Gladstone
2 years
After traveling with my wife for 6 mo straight in 2019, I came back home wanting more of 2 things: 1. Tighter community (offline) 2. Time outside Owning a landscaping company helps with #2 , but #1 is still very difficult for me to be proactive about.
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@glad_cap
James | Gladstone
2 years
SMB twitter, what is your “daily driver” shoe? Saw @StrongpointRich and @RegZeller give Danner lots of love. I’m on 3rd pair of Salomon x ultra 3 gtx but thinking of switching up
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James | Gladstone
4 years
@huntermarkj @sweatystartup @laughridge @StrongpointRich This is the hardest step so far for me... when do you typically dig in at the GL level to the financials? Pre-offer or during DD stage? Here's what I've scrubbed so far, but definitely need some more convo's w/ owner and mgr. Just want to time my harassments correctly
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James | Gladstone
2 years
Some business-focused reflections for the month (framework from @dickiebush ) 1. What were my biggest wins? - Letting go of some high-headache employees - Getting books in a better spot
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James | Gladstone
2 years
@SMB_Attorney The thing that works best for me is having at least 1-2 fitness events per year to train for. Even if you can't have a consistent training schedule, it forces you to not fall too far off the wagon.
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@glad_cap
James | Gladstone
2 years
If you're moving but holding onto your house / condo as a rental... Put a home equity line of credit on your house BEFORE you move out. Costs nothing and significantly easier to do while your home is a primary residence. Never know when you'll need cash.
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James | Gladstone
3 years
2. CASH Have way more cash available than you think you need, and get started while you still have W2 income. I signed up for ~150k in personal LOC's with local banks, and saved up 3x the cash I thought I would need to close on the business and fund initial ops.
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James | Gladstone
3 years
Do you have a finance degree and 1/2 of an MBA, 10 years of corporate consulting experience but still have no idea how bookkeeping works? Pumped to see how this project evolves. No doubt going 🚀🚀🚀 with ⁦ @baldridgecpa ⁩ and @joshuamschultz ⁩ leading the charge!
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