Riki's Cloak and Dagger allows him to scout and place wards without revealing himself. Making him a viable roamer or support hero.
Riki is exceptional at ganking lone heroes and picking them off one by one. He can snowball easily through just getting lots of kills even without farm. Try to get kills before the enemy starts grouping up, so they cannot punish you with detection items.
Riki is an attribute-based carry, thanks to Cloak and Dagger's backstab damage. This means that it continues to get stronger and stronger as the game goes on, as long as you continue to farm, gank, and purchase the right items.
Because of this, Diffusal Blade should be your first core item completed, it gives everything Riki needs: the agility scales well with and the active slow helps keep enemies within Smoke Screen, which is your main ganking combo.
Do not walk straight up to enemies and deep into enemy territory and expect never to die. If they have any kind of detection (e.g. Sentry Ward), then Riki dies very quickly.
As a result of this, make a habit of constantly checking the enemy's inventory for revealing items.
Be wary around more durable enemy heroes. Spell immunity from Black King Bar allows enemies to ignore Smoke Screen and fight Riki, ignoring his backstab damage.
Riki is a key hero to catch slippery foes and heroes that are heavily reliant on their own active skills since he can approach without detection and use smoke to prevent them from using escape spells, so it is wise to pick him as a counter pick to many heroes like Slark, Juggernaut, Anti-Mage, Weaver or Storm Spirit. However, be careful of enemies carrying escape items, like Force Staff, Glimmer Cape, Blink Dagger or Shadow Blade/Silver Edge.
Always scout the enemy jungle once in a while, you may encounter some enemy farming alone for an easy kill, also help high mobility heroes like Spirit Breaker or Nature's Prophet to set up a gank.
Do not be afraid of enemies carrying Gem of True Sight, track down their movement and wait, sooner or later they are going to end up alone and when this happens do not hesitate, use the fog of war and approach them from the sides, go for the kill and recover the Gem.
Riki requires a lot of map knowledge as some supports or players place sentry wards in obvious position. Knowing heroes who carry dust, knowing the range of the sentry detection and knowing hot spots for sentry placement can increase your overall survivability in the game
If Riki's enemies do not have any form of detection, the invisibility will let Riki escape with ease and roam freely.
If they do, Riki has to rely on his cunning and speed in order to get the drop on enemies, and get out alive.
You can take Cloak and Dagger as your first skill point and easily take the first Bounty Rune in either side of the river, unless the enemy has any form of detection.
Cloak and Dagger also enables him to deal incredible damage from behind based on a multiplier of his agility.
Since good supports always stay behind, you can flank the enemy team coming around from there and catching the supports as soon as a teamfight begins and the enemy team is so busy fighting yours that they do not realize that their supports are already dead. This strategy also applies to enemy initiators with game-changing ultimates like Enigma or Magnus, as a good interruption can set victory in critical situations.
A well-organized team will often buy Sentry Ward to keep vision of Riki. You may want to take it upon yourself to de-ward your lane if needs be; if you are without a support, or so that your support can concentrate on other items.
Later in the game, you can use Tricks of the Trade after Blink Strike to initiate, then safely Blink Strike again to escape enemies waiting for you.
Tricks of the Trade may be combined with cleave from Battle Fury or Empower to devastate closely grouped enemies.
Tricks of the Trade turns Riki invulnerable and hidden for a maximum of 5 seconds. Do not be afraid to use the skill to avoid dying from spells such as Assassinate.
Items
Starting items:
Tangos and Healing Salve compensate for poor starting HP, allowing you to stay longer in the lane and reach level 6 sooner.
Slippers of Agility and three Iron Branches to increase early damage and both health and mana regeneration. The branches also set up for the wand later.
Early game:
Magic Stick replaces your consumables with an alternative source of recovery, particularly if the enemy team includes heroes that rely on abilities.
Boots of Speed provide movement speed, allowing Riki to keep pace with fleeing heroes while Blink Strike is on cooldown.
Orb of Venom helps secure kills with its movement slow and helps compensate for Riki's own horrible movement speed.
Mid game:
Power Treads give Riki increased attack speed as well as a further bonus to attributes.
Magic Wand is an obvious upgrade from the Magic Stick and Iron Branches purchased earlier, freeing up inventory slots while retaining the attribute bonuses and healing ability.
Diffusal Blade provides a way to slow fleeing heroes, keeping them in Smoke Screen, as well as burning mana from casters for extra damage. It also boosts agility which will increase Cloak and Dagger's backstab damage.
Late game:
Butterfly provides a huge increase in both survivability and damage, as well as attack speed. It also boosts your agility which scales well with Cloak and Dagger's backstab damage.
Abyssal Blade allows Riki to cancel TPs with stun and bash, as well as continuing to lock-down opponents once they have acquired Black King Bar.
Situational items:
Drum of Endurance is a good early/mid game pickup, makes everyone faster and gives you stats, coupled with Orb of Venom for a better chasing power.
Black King Bar allows Riki to effectively fight in team-fights and get kills against opponents that have strong disables.
Sange and Yasha give great attribute bonuses, as well as an extra slow on top of Diffusal Blade.
Eye of Skadi gives attributes across the board as well as a flat health and mana pool bonus, allowing Riki to take more hits, deal more damage and use more abilities. It also gives a powerful, spell immunity piercing slow that will prevent your target from escaping.
Blink Dagger allows Riki to initiate using Blink Strike and Tricks of the Trade, then safely blinking away just before Tricks of the Trade finishes.
Manta Style can be used to dispel debuffs, including Dust of Appearance, as it's the only source of dispel which has beneficial stats for Riki.
Maelstrom can proc with Tricks of the Trade, but only up to once per strike due to the item's internal cooldown of 0.2 seconds. Can be upgraded to Mjollnir for higher damage.
Desolator can be used with Tricks of the Trade to hit multiple targets and reduce their armor, causing it to essentially be a multiple target Medallion of Courage.
Aghanim's Scepter allows Riki to use longer duration Tricks of the Trade inside an ally, boosting survivability and damage output.